Method for producing primary and secondary amine compounds

Abstract

To provide practical production methods for primary and secondary amine compounds that can selectively synthesize primary and secondary amine compounds from aldehyde compounds and demonstrate excellent reaction operativity.SOLUTION: The present invention discloses methods for producing primary and secondary amine compounds by combining the reductive amination reaction of an aldehyde compound by an organic iridium complex catalyst with a specific amino alcohol as an amine source and the oxidative deprotection reaction.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a practical method for producing primary and secondary amine compounds. [Background technology]

[0002] As a method for synthesizing a primary or secondary amine compound from an aldehyde compound, a synthesis method in which the aldehyde compound is reduced in the presence of the corresponding starting amine compound is generally known (Non-Patent Documents 1 and 2). However, in this method, the nucleophilicity of the generated primary or secondary amine compound is higher than that of the starting amine compound, and it is difficult to actually suppress the further reaction of the generated primary or secondary amine compound to produce undesired secondary and / or tertiary amine compounds as by-products, making this method not a practical method.

[0003] As a method for increasing the selectivity to primary amine compounds, a method is known in which an oxime is first synthesized from an aldehyde compound and hydroxylamine, and then catalytically hydrogenated to produce a primary amine compound (Patent Document 1). However, this method is not a simple method because it is necessary to prepare an oxime in advance, and the reduction reaction of the oxime is carried out under a high-pressure hydrogen atmosphere of 1 MPa, and a special reaction vessel such as a pressure-resistant kettle is required. In addition, a method is also known in which a carbamate derivative is synthesized from an aldehyde compound and a carbamate compound by a reductive amination reaction using trichlorosilane as a reducing agent, and then the carbamate derivative is deprotected by, for example, hydrolysis to produce a primary amine compound (Patent Document 2). However, this method is not a simple method because it requires trichlorosilane as a reducing agent, which has a low boiling point and is unstable to moisture, and is difficult to handle. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] JP 2000-273069 A [Patent Document 2] Patent No. 4212466 [Non-patent literature]

[0005] [Non-Patent Document 1] J. Org. Chem. 1996, 61, 3849. [Non-Patent Document 2] J. Org. Chem. 2010,75,5470. Summary of the Invention [Problem to be solved by the invention]

[0006] An object of the present invention is to provide a practical method for producing primary and secondary amine compounds, which can selectively synthesize primary and secondary amine compounds from aldehyde compounds and has excellent reaction operability. [Means for solving the problem]

[0007] In the course of studying the reductive amination reaction between a carbonyl compound and an amine compound, the present inventors have encountered the problem that in a method of reductive amination from an aldehyde compound using an ammonia equivalent as an amine source, it is difficult to selectively synthesize a primary amine compound due to problems such as over-alkylation, etc. In addition, in the case of a specific aldehyde compound, even in a method of reductive amination using a primary amine such as methylamine as an amine source, it may be difficult to selectively synthesize a secondary amine compound due to over-alkylation.

[0008] In the course of intensive research, the inventors discovered that by using a specific aminoalcohol as an amine source and an organic iridium complex as a catalyst, the product amine having a 2-hydroxyethyl skeleton on the nitrogen atom is less likely to undergo overalkylation due to its bulkiness, and secondary or tertiary amine compounds can be selectively synthesized. Furthermore, the amine compound having a 2-hydroxyethyl skeleton on the nitrogen atom synthesized from this aminoalcohol can be oxidatively deprotected by a simple operation without requiring a special reaction vessel such as a pressure-resistant kettle, and therefore the inventors discovered that by combining these, the desired primary or secondary amine compound can be selectively synthesized, leading to the completion of the present invention.

[0009] That is, the present invention relates to the following. [1] A method for producing a primary or secondary amine compound, comprising the steps of: The following general formula (1) [ka] In the formula, R 1 is a hydrogen atom, a C1-C20 saturated or unsaturated hydrocarbon group in which one or more hydrogen atoms may be substituted with a substituent W, an aryl group having 6 to 22 ring members in which a carbon atom may be substituted with a heteroatom, or a heterocyclyl group having 3 to 20 ring members, W is a C1-C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by heteroatoms, a heterocyclyl group having 3 to 20 ring members, a C1-C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1-20 sulfenyl group, a C1-20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1-C20 fluoroalkyl group, two or more Ws may be joined together to form one or more rings, Ra, Rb and Rc are the same or different and each represent a hydrogen atom, a C1-C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, an aralkyl group having 6 to 20 ring members, a heteroaralkyl group having 6 to 20 ring members, an alkylaryl group having 6 to 20 ring members, or an alkylheteroaryl group having 6 to 20 ring members; R 2 , R 3 , R 4 and R 5 are the same or different and each is a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, or an aryl group having 6 to 22 ring members in which a carbon atom may be replaced by a heteroatom, n is 1 or 2, If n is 2, R 1 does not exist, and an amino alcohol represented by the formula: The following general formula (2) [ka] In the formula, R 6 represents a C1-C20 saturated or unsaturated hydrocarbon group in which one or more hydrogen atoms may be substituted by the substituent W, an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1-C20 carboxyl group, an ester group bonded at a C1-C20 carbon atom, an amide group bonded at a C1-C20 carbon atom, or a C1-C20 acyl group, Ra, Rb and Rc have the same meanings as above. and an aldehyde represented by The following general formula (3) [ka] In the formula, Ar is a cyclopentadienyl group in which one or more hydrogen atoms may be replaced by the aforementioned substituent W; X is a hydride group or an anionic group; R 7 and R 8are the same or different and each represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to 20 sulfenyl group, a C1 to 20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, one or more hydrogen atoms of these groups may be replaced by the substituent W, Ra, Rb and Rc have the same meanings as above, j and k are the same or different and are integers from 0 to 3; R 7 or R 8 a carbon atom in the quinoline ring to which is not attached may be replaced by a nitrogen atom, If j is 2 or more, R is 2 or more 7 may be joined together to form one or more rings, The following general formula (4) [ka] In the formula, Ar, X and R 7 has the same meaning as above, R 9represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by heteroatoms, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 sulfenyl group, a C1 to C20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, one or more hydrogen atoms of these groups may be replaced by the substituent W, Ra, Rb and Rc have the same meanings as above, l is an integer from 0 to 4, R 7 a carbon atom in the pyridine ring to which is not bonded may be replaced by a nitrogen atom, If l is 2 or more, R is 2 or more 7 may be joined together to form one or more rings, The following general formula (5) [ka] In the formula, Ar, X, R 7 , l has the same meaning as above, R 10 and R 11 are the same or different and each represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to 20 sulfenyl group, a C1 to 20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, one or more hydrogen atoms of these groups may be replaced by the substituent W, R 10 and R 11 and may be taken together to form a ring, R 12 is a C1 to C20 sulfonyl group, -C(=O)-Ra or -C(=O)-NRaRb, and one or more hydrogen atoms of these groups may be substituted by the substituent W, Ra, Rb and Rc have the same meanings as above, R 7 a carbon atom in the pyridine ring to which is not bonded may be replaced by a nitrogen atom, If l is 2 or more, R is 2 or more 7 may be joined together to form one or more rings, or The following general formula (6) [ka] In the formula, Ar and X have the same meanings as above. A is a saturated or unsaturated nitrogen-containing heterocyclic carbene containing at least two nitrogen atoms, in which one or more hydrogen atoms may be substituted by the substituent W; R 13 , R 14 , R 15 ,R 16 and R 17 are the same or different and each represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to 20 sulfenyl group, a C1 to 20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, one or more hydrogen atoms of these groups may be replaced by the substituent W, R 18represents a C1 to C20 sulfonyl group, -C(=O)-Ra, -C(=O)-ORa, -C(=O)-NRaRb, -C(=S)-NRaRb, a C1 to C20 fluoroalkyl group, or an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, and one or more hydrogen atoms of these groups may be substituted by the substituent W, Ra, Rb and Rc have the same meanings as above. With a hydrogen donor compound in the presence of an organic iridium compound represented by the formula: The reaction product is represented by the following general formula (A): [ka] In the formula, R 2 , R 3 , R 4 , R 5 and n has the same meaning as in general formula (1). a step of oxidatively deprotecting the moiety represented by The method, comprising:

[0010] [2] A method for producing a primary or secondary amine compound, comprising the steps of: The following general formula (1) [ka] In the formula, R 1 is a hydrogen atom, a C1-C20 saturated or unsaturated hydrocarbon group in which one or more hydrogen atoms may be substituted with a substituent W, an aryl group having 6 to 22 ring members in which a carbon atom may be substituted with a heteroatom, or a heterocyclyl group having 3 to 20 ring members, W is a C1-C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by heteroatoms, a heterocyclyl group having 3 to 20 ring members, a C1-C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1-20 sulfenyl group, a C1-20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1-C20 fluoroalkyl group, two or more Ws may be joined together to form one or more rings, Ra, Rb and Rc are the same or different and each represent a hydrogen atom, a C1-C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, an aralkyl group having 6 to 20 ring members, a heteroaralkyl group having 6 to 20 ring members, an alkylaryl group having 6 to 20 ring members, or an alkylheteroaryl group having 6 to 20 ring members; R 2 , R 3 , R 4 and R 5 are the same or different and each is a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, or an aryl group having 6 to 22 ring members in which a carbon atom may be replaced by a heteroatom, n is 1 or 2, If n is 2, R 1 does not exist, and an amino alcohol represented by the formula: The following general formula (2) [ka] In the formula, R 6represents a C1-C20 saturated or unsaturated hydrocarbon group in which one or more hydrogen atoms may be substituted by the substituent W, an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1-C20 carboxyl group, an ester group bonded at a C1-C20 carbon atom, an amide group bonded at a C1-C20 carbon atom, or a C1-C20 acyl group, Ra, Rb and Rc have the same meanings as above. and an aldehyde represented by The following general formula (7) [ka] In the formula, Ar is a cyclopentadienyl group in which one or more hydrogen atoms may be replaced by the aforementioned substituent W; X is a hydride group or an anionic group; and an organic iridium compound represented by the formula: The following general formula (8) [ka] In the formula, R 7 and R 8 are the same or different and each represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to 20 sulfenyl group, a C1 to 20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, one or more hydrogen atoms of these groups may be replaced by the substituent W, Ra, Rb and Rc have the same meanings as above, j and k are the same or different and are integers from 0 to 3; R 7 or R8 a carbon atom in the quinoline ring to which is not attached may be replaced by a nitrogen atom, If j is 2 or more, R is 2 or more 7 may be joined together to form one or more rings, The following general formula (9) [ka] In the formula, R 7 has the same meaning as above, R 9 represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by heteroatoms, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 sulfenyl group, a C1 to C20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, one or more hydrogen atoms of these groups may be replaced by the substituent W, Ra, Rb and Rc have the same meanings as above, l is an integer from 0 to 4, R 7 a carbon atom in the pyridine ring to which is not bonded may be replaced by a nitrogen atom, If l is 2 or more, R is 2 or more 7 may be joined together to form one or more rings, The following general formula (10) [ka] In the formula, R 7 and l has the same meaning as above, R 10 and R 11are the same or different and each represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to 20 sulfenyl group, a C1 to 20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, one or more hydrogen atoms of these groups may be replaced by the substituent W, R 10 and R 11 and may be taken together to form a ring, R 12 is a C1 to C20 sulfonyl group, -C(=O)-Ra or -C(=O)-NRaRb, and one or more hydrogen atoms of these groups may be substituted by the substituent W, Ra, Rb and Rc have the same meanings as above, R 7 a carbon atom in the pyridine ring to which is not bonded may be replaced by a nitrogen atom, If l is 2 or more, R is 2 or more 7 may be joined together to form one or more rings, or The following general formula (11) [ka] In the formula, R 13 , R 14 , R 15 ,R 16 and R 17are the same or different and each represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to 20 sulfenyl group, a C1 to 20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, one or more hydrogen atoms of these groups may be replaced by the substituent W, R 18 represents a C1 to C20 sulfonyl group, -C(=O)-Ra, -C(=O)-ORa, -C(=O)-NRaRb, -C(=S)-NRaRb, a C1 to C20 fluoroalkyl group, or an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, and one or more hydrogen atoms of these groups may be replaced by the substituent W. A' is a saturated or unsaturated nitrogen-containing heterocyclic carbene precursor containing at least two nitrogen atoms, in which one or more hydrogen atoms may be substituted with the substituent W; Ra, Rb and Rc have the same meanings as above. Y is an anionic group; with a hydrogen donor compound in the presence of an organic compound represented by the formula: The reaction product is represented by the following general formula (A): [ka] In the formula, R 2 , R 3 , R 4 , R 5 and n has the same meaning as in general formula (1). a step of oxidatively deprotecting the moiety represented by The method, comprising:

[0011] [3] A method for producing primary and secondary amine compounds, comprising the steps of: The following general formula (1) [ka] In the formula, R 1 is a hydrogen atom, a C1-C20 saturated or unsaturated hydrocarbon group in which one or more hydrogen atoms may be substituted with a substituent W, an aryl group having 6 to 22 ring members in which a carbon atom may be substituted with a heteroatom, or a heterocyclyl group having 3 to 20 ring members, W is a C1-C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by heteroatoms, a heterocyclyl group having 3 to 20 ring members, a C1-C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1-20 sulfenyl group, a C1-20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1-C20 fluoroalkyl group, two or more Ws may be joined together to form one or more rings, Ra, Rb and Rc are the same or different and each represent a hydrogen atom, a C1-C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, an aralkyl group having 6 to 20 ring members, a heteroaralkyl group having 6 to 20 ring members, an alkylaryl group having 6 to 20 ring members, or an alkylheteroaryl group having 6 to 20 ring members; R 2 , R 3 , R 4 and R 5 are the same or different and each is a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, or an aryl group having 6 to 22 ring members in which a carbon atom may be replaced by a heteroatom, n is 1 or 2, If n is 2, R 1 does not exist, and an amino alcohol represented by the formula: The following general formula (2) [ka] In the formula, R 6 represents a C1-C20 saturated or unsaturated hydrocarbon group in which one or more hydrogen atoms may be substituted by the substituent W, an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1-C20 carboxyl group, an ester group bonded at a C1-C20 carbon atom, an amide group bonded at a C1-C20 carbon atom, or a C1-C20 acyl group, Ra, Rb and Rc have the same meanings as above. A hemiaminal ether, imine, or enamine prepared from an aldehyde represented by the formula: The following general formula (3) [ka] In the formula, Ar is a cyclopentadienyl group in which one or more hydrogen atoms may be replaced by the aforementioned substituent W; X is a hydride group or an anionic group; R 7 and R 8 are the same or different and each represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to 20 sulfenyl group, a C1 to 20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, one or more hydrogen atoms of these groups may be replaced by the substituent W, Ra, Rb and Rc have the same meanings as above, j and k are the same or different and are integers from 0 to 3; R 7 or R 8 a carbon atom in the quinoline ring to which is not attached may be replaced by a nitrogen atom, If j is 2 or more, R is 2 or more 7 may be joined together to form one or more rings, The following general formula (4) [ka] In the formula, Ar, X and R 7 has the same meaning as above, R 9 represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by heteroatoms, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 sulfenyl group, a C1 to C20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, one or more hydrogen atoms of these groups may be replaced by the substituent W, Ra, Rb and Rc have the same meanings as above, l is an integer from 0 to 4, R 7 a carbon atom in the pyridine ring to which is not bonded may be replaced by a nitrogen atom, If l is 2 or more, R is 2 or more 7 may be joined together to form one or more rings, The following general formula (5) [ka] In the formula, Ar, X, R 7 , l has the same meaning as above, R 10 and R 11are the same or different and each represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to 20 sulfenyl group, a C1 to 20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, one or more hydrogen atoms of these groups may be replaced by the substituent W, R 10 and R 11 and may be taken together to form a ring, R 12 is a C1 to C20 sulfonyl group, -C(=O)-Ra or -C(=O)-NRaRb, and one or more hydrogen atoms of these groups may be substituted by the substituent W, Ra, Rb and Rc have the same meanings as above, R 7 a carbon atom in the pyridine ring to which is not bonded may be replaced by a nitrogen atom, If l is 2 or more, R is 2 or more 7 may be joined together to form one or more rings, or The following general formula (6) [ka] In the formula, Ar and X have the same meanings as above. A is a saturated or unsaturated nitrogen-containing heterocyclic carbene containing at least two nitrogen atoms, in which one or more hydrogen atoms may be substituted by the substituent W; R 13 , R 14 , R 15 ,R 16 and R 17are the same or different and each represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to 20 sulfenyl group, a C1 to 20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, one or more hydrogen atoms of these groups may be replaced by the substituent W, R 18 represents a C1 to C20 sulfonyl group, -C(=O)-Ra, -C(=O)-ORa, -C(=O)-NRaRb, -C(=S)-NRaRb, a C1 to C20 fluoroalkyl group, or an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, and one or more hydrogen atoms of these groups may be substituted by the substituent W, Ra, Rb and Rc have the same meanings as above. With a hydrogen donor compound in the presence of an organic iridium compound represented by the formula: The reaction product is represented by the following general formula (A): [ka] In the formula, R 2 , R 3 , R 4 , R 5 and n has the same meaning as in general formula (1). a step of oxidatively deprotecting the moiety represented by The method, comprising:

[0012] [4] A method for producing primary and secondary amine compounds, comprising the steps of: The following general formula (1) [ka] In the formula, R 1 is a hydrogen atom, a C1-C20 saturated or unsaturated hydrocarbon group in which one or more hydrogen atoms may be substituted with a substituent W, an aryl group having 6 to 22 ring members in which a carbon atom may be substituted with a heteroatom, or a heterocyclyl group having 3 to 20 ring members, W is a C1-C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by heteroatoms, a heterocyclyl group having 3 to 20 ring members, a C1-C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1-20 sulfenyl group, a C1-20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1-C20 fluoroalkyl group, two or more Ws may be joined together to form one or more rings, Ra, Rb and Rc are the same or different and each represent a hydrogen atom, a C1-C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, an aralkyl group having 6 to 20 ring members, a heteroaralkyl group having 6 to 20 ring members, an alkylaryl group having 6 to 20 ring members, or an alkylheteroaryl group having 6 to 20 ring members; R 2 , R 3 , R 4 and R 5 are the same or different and each is a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, or an aryl group having 6 to 22 ring members in which a carbon atom may be replaced by a heteroatom, n is 1 or 2, If n is 2, R 1 is not present, and The following general formula (2) [ka] In the formula, R 6represents a C1-C20 saturated or unsaturated hydrocarbon group in which one or more hydrogen atoms may be substituted by the substituent W, an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1-C20 carboxyl group, an ester group bonded at a C1-C20 carbon atom, an amide group bonded at a C1-C20 carbon atom, or a C1-C20 acyl group, Ra, Rb and Rc have the same meanings as above. A hemiaminal ether, imine, or enamine prepared from an aldehyde represented by the formula: The following general formula (7) [ka] During the ceremony, Ar is a cyclopentadienyl group in which one or more hydrogen atoms may be replaced by the aforementioned substituent W; X is a hydride group or an anionic group; and an organic iridium compound represented by the formula: The following general formula (8) [ka] In the formula, R 7 and R 8 are the same or different and each represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to 20 sulfenyl group, a C1 to 20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, one or more hydrogen atoms of these groups may be replaced by the substituent W, Ra, Rb and Rc have the same meanings as above, j and k are the same or different and are integers from 0 to 3; R 7 or R 8 a carbon atom in the quinoline ring to which is not attached may be replaced by a nitrogen atom, If j is 2 or more, R is 2 or more 7 may be joined together to form one or more rings, The following general formula (9) [ka] In the formula, R 7 has the same meaning as above, R 9 represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by heteroatoms, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 sulfenyl group, a C1 to C20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, one or more hydrogen atoms of these groups may be replaced by the substituent W, Ra, Rb and Rc have the same meanings as above, l is an integer from 0 to 4, R 7 a carbon atom in the pyridine ring to which is not bonded may be replaced by a nitrogen atom, If l is 2 or more, R is 2 or more 7 may be joined together to form one or more rings, The following general formula (10) [ka] During the ceremony, R 7 and l has the same meaning as above, R 10 and R11 are the same or different and each represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to 20 sulfenyl group, a C1 to 20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, one or more hydrogen atoms of these groups may be replaced by the substituent W, R 10 and R 11 and may be taken together to form a ring, R 12 is a C1 to C20 sulfonyl group, -C(=O)-Ra or -C(=O)-NRaRb, and one or more hydrogen atoms of these groups may be substituted by the substituent W, Ra, Rb and Rc have the same meanings as above, R 7 a carbon atom in the pyridine ring to which is not bonded may be replaced by a nitrogen atom, If l is 2 or more, R is 2 or more 7 may be joined together to form one or more rings, or The following general formula (11) [ka] In the formula, R 13 , R 14 , R 15 ,R 16 and R 17are the same or different and each represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to 20 sulfenyl group, a C1 to 20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, one or more hydrogen atoms of these groups may be replaced by the substituent W, R 18 represents a C1 to C20 sulfonyl group, -C(=O)-Ra, -C(=O)-ORa, -C(=O)-NRaRb, -C(=S)-NRaRb, a C1 to C20 fluoroalkyl group, or an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, and one or more hydrogen atoms of these groups may be replaced by the substituent W. A' is a saturated or unsaturated nitrogen-containing heterocyclic carbene precursor containing at least two nitrogen atoms, in which one or more hydrogen atoms may be substituted with the substituent W; Ra, Rb and Rc have the same meanings as above. Y is an anionic group; with a hydrogen donor compound in the presence of an organic compound represented by the formula: The reaction product is represented by the following general formula (A): [ka] In the formula, R 2 , R 3 , R 4 , R 5 and n has the same meaning as in general formula (1). a step of oxidatively deprotecting the moiety represented by The method, comprising:

[0013] [5] The method according to any one of the above [1] to [4], wherein the aminoalcohol represented by the general formula (1) is 2-aminoethanol, 2-amino-1-propanol, 2-amino-1-butanol, valinol or phenylglycinol. [6] The method according to any one of the above [1] to [5], wherein the oxidative deprotection is carried out using periodic acid, a periodate salt or lead tetraacetate as an oxidizing agent.

[0014] [7] The method according to any one of the above [1] to [6], wherein the hydrogen-donating compound is formic acid or a formate. Effect of the Invention

[0015] According to the present invention, by using a specific aminoalcohol as an amine source and an organic iridium complex as a catalyst, the reductive amination reaction of an aldehyde compound proceeds without causing overalkylation. Furthermore, by using a specific aminoalcohol, a substituent having a 2-hydroxyethyl skeleton on the nitrogen is oxidatively deprotected by a simple operation, and a primary or secondary amine compound can be selectively synthesized. This makes it possible to selectively produce a primary or secondary amine compound, which was difficult in the conventional reductive amination reaction of an aldehyde compound using an ammonia equivalent or a primary amine compound as an amine source. In addition, in the reduction reaction of an oxime using hydroxylamine as an amine source, the reaction is carried out under a high-pressure hydrogen atmosphere, so a special reaction vessel such as a pressure-resistant kettle is required, whereas the present invention makes it possible to carry out both the reduction reaction and the deprotection reaction with a simple operation without requiring a special reaction vessel. [Brief description of the drawings]

[0016] [Figure 1] 1 is a reaction formula showing an example of the production method of the present invention. [Diagram 2] 1 is a structural formula showing an example of an iridium compound used in the production method of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0017] The present invention will be described in detail below based on preferred embodiments. The present invention is a method for producing a primary or secondary amine compound, comprising the steps of reacting an aminoalcohol represented by the general formula (1) and an aldehyde compound represented by the general formula (2) with a hydrogen-donating compound in the presence of an organic iridium compound represented by the general formula (3), general formula (4), general formula (5) or general formula (6), and oxidatively deprotecting a substituent having a 2-hydroxyethyl skeleton on the nitrogen. In the present invention, the "substituent having a 2-hydroxyethyl skeleton on the nitrogen atom" means the moiety represented by the above general formula (A).

[0018] The amino alcohol used in the present invention is represented by the general formula (1): [ka] It is expressed as: In the formula, R 1 is a hydrogen atom, a C1-C20 saturated or unsaturated hydrocarbon group in which one or more hydrogen atoms may be substituted with a substituent W, an aryl group having 6 to 22 ring members in which a carbon atom may be substituted with a heteroatom, or a heterocyclyl group having 3 to 20 ring members. In this specification, the term "hydrocarbon group" refers to a group consisting of a carbon skeleton and hydrogen atoms bonded thereto, and includes saturated or unsaturated linear or cyclic hydrocarbon groups. For example, examples of saturated or unsaturated linear hydrocarbon groups include linear or branched alkyl groups, alkenyl groups, and alkynyl groups, while examples of saturated or unsaturated cyclic hydrocarbon groups include cycloalkyl groups, cycloalkenyl groups, cycloalkynyl groups, aryl groups, and groups in which one or more hydrogen atoms of these cyclic hydrocarbon groups are substituted with saturated or unsaturated linear hydrocarbon groups, such as aralkyl groups and arylalkyl groups.

[0019] In this specification, the alkyl groups, alkenyl groups and alkynyl groups include those having straight or branched chains. The substituent W is a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 sulfenyl group, a C1 to C20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group.

[0020] In addition, Ra, Rb and Rc are the same or different and each represent a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, an aralkyl group having 6 to 20 ring members, a heteroaralkyl group having 6 to 20 ring members, an alkylaryl group having 6 to 20 ring members, or an alkylheteroaryl group having 6 to 20 ring members. Specific examples of Ra, Rb, and Rc include, but are not limited to, a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, an n-butyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a cyclopentyl group, an n-hexyl group, a cyclohexyl group, a cyclohexylene group, a vinyl group, a propenyl group, a butenyl group, a phenyl group, a toluyl group, a xylyl group, a naphthyl group, a pyridyl group, a furanyl group, a thienyl group, a pyrrolidyl group, a piperidyl group, a benzyl group, and a pyridylmethyl group.

[0021] Specific examples of W include, but are not limited to, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, an n-butyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a cyclopentyl group, an n-hexyl group, a cyclohexyl group, a benzyl group, a cyclohexylene group, a vinyl group, a propenyl group, a butenyl group, a phenyl group, a toluyl group, a xylyl group, a naphthyl group, a pyridyl group, a furanyl group, a thienyl group, a pyrrolidyl group, a piperidyl group, a methyl group, a phenyl ... butoxy group, ethoxy group, propoxy group, benzyloxy group, acetyl group, propionyl group, cyclohexanecarbonyl group, benzoyl group, methoxycarbonyl group, ethoxycarbonyl group, tert-butoxycarbonyl group, benzyloxycarbonyl group, acetyloxy group, benzoyloxy group, hydroxyl group, methylamino group, ethylamino group, n-propylamino group, isopropylamino group, dimethylamino group, diethylamino group, di-n-propylamino group, diisopropylamino group,

[0022] Examples of the alkyl group include a carbamoyl group, an N-methylcarbamoyl group, an N,N-dimethylcarbamoyl group, an N-acetylamino group, an N-methyl-N-acetylamino group, an N-benzoylamino group, an N-methyl-N-benzoylamino group, an N-hydroxylamino group, an N-methoxyamino group, a nitro group, a cyano group, a diphenylphosphino group, a dicyclohexylphosphino group, a cyclopropylphosphino group, a cyclobutylphosphino group, a cyclopentylphosphino group, a cyclohexylphosphino group, a methanesulfenyl group, an ethanesulfenyl group, a methanesulfonyl group, an ethanesulfonyl group, a benzenesulfonyl group, a p-toluenesulfonyl group, a trifluoromethanesulfonyl group, a sulfo group, a mercapto group, a methylsilyl group, a dimethylsilyl group, a trimethylsilyl group, a fluorine group, a bromine group, a chlorine group, an iodine group, and a trifluoromethyl group.

[0023] In addition, two or more Ws may join together to form one or more rings. Specific examples of the rings formed include, but are not limited to, cycloalkanes such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, and cycloheptane; aromatic rings such as benzene, naphthalene, and anthracene; aryl-fused cycloalkanes such as indane and tetralin; heteroaromatic rings such as pyrrole, pyridine, pyrazine, pyrimidine, pyridazine, triazine, thiophene, furan, imidazole, oxazole, thiazole, quinoline, benzothiophene, and benzofuran; heterocyclic compounds such as tetrahydrofuran, tetrahydropyran, pyrrolidine, piperidine, coumaran, chroman, indoline, and tetrahydroquinoline; and the like. One or more hydrogen atoms of these rings may be further substituted with a substituent W.

[0024] R 1 Specific examples of the alkyl group include, but are not limited to, a hydrogen atom; straight-chain or branched-chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, or dodecyl; fluoroalkyl groups such as a trifluoromethyl group; cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl; unsaturated hydrocarbons such as vinyl or allyl; aralkyl groups such as benzyl; monocyclic or polycyclic aryl groups such as phenyl, naphthyl, anthryl, phenanthryl, or indenyl; and monocyclic or polycyclic heterocyclyl groups such as thienyl, furyl, pyranyl, xanthenyl, pyridyl, pyrrolyl, imidazolinyl, indolyl, carbazoyl, phenanthronyl, pyrrolidyl, or piperidyl, and preferably a hydrogen atom.

[0025] R 2 , R 3 , R 4 and R 5are the same or different and are a hydrogen atom, a C1-C20 saturated or unsaturated hydrocarbon group, or an aryl group having 6 to 22 ring members in which a carbon atom may be replaced with a heteroatom. Specific examples include, but are not limited to, a hydrogen atom and a hydrocarbon group such as an alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl, heteroaralkyl, aryl, and heteroaryl. Preferred are a hydrogen atom, a saturated chain hydrocarbon group, an aralkyl group, a heteroaralkyl group, an aromatic hydrocarbon group, or a heteroaromatic hydrocarbon group, more preferred are a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, an isobutyl group, a 2-butyl group, a tert-butyl group, a benzyl group, a (1H-imidazol-4-yl)methyl group, a (3-indolyl)methyl group, or a phenyl group, and particularly preferred are a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, and a phenyl group. n is 1 or 2, and when n is 2, R 1 means not present. Preferably, n is 1.

[0026] More specifically, the aminoalcohol represented by the general formula (1) is, for example, 2-aminoethanol, 2-amino-1-propanol, 2-amino-1-butanol, valinol, leucinol, isoleucinol, tert-leucinol, phenylalaninol, or phenylglycinol, and preferably 2-aminoethanol, 2-amino-1-propanol, 2-amino-1-butanol, valinol, or phenylglycinol.

[0027] The aldehyde compound is represented by the general formula (2) [ka] It is expressed as: In the formula, R 6is a C1-C20 saturated or unsaturated hydrocarbon group in which one or more hydrogen atoms may be substituted with the substituent W, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced with heteroatoms, a heterocyclyl group having 3 to 20 ring members, a C1-C20 carboxyl group, an ester group bonded at a C1-C20 carbon atom, an amide group bonded at a C1-C20 carbon atom, or a C1-C20 acyl group.

[0028] Specific examples include, but are not limited to, linear or branched alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl; fluoroalkyl groups such as trifluoromethyl; cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl; unsaturated hydrocarbons such as vinyl and allyl; aralkyl groups such as benzyl; phenyl, naphthyl, anthryl, phenanthryl, and indenyl groups. Examples of the substituent include monocyclic or polycyclic aryl groups, monocyclic or polycyclic heterocyclyl groups such as thienyl, furyl, pyranyl, xanthenyl, pyridyl, pyrrolyl, imidazolinyl, indolyl, carbazoyl, phenanthronyl, pyrrolidyl, and piperidyl, ester groups such as ferrocenyl, carboxyl, methoxycarbonyl, and ethoxycarbonyl, amide groups such as carbamoyl, N-methylcarbamoyl, and N,N-dimethylcarbamoyl, and acyl groups such as acetyl and benzoyl. Preferred are branched alkyl groups, aryl groups, and heterocyclyl groups, which may have the substituent W.

[0029] In addition, in the present invention, a primary or secondary amine compound may be produced by reacting a hemiaminal ether, imine, or enamine prepared from an aminoalcohol represented by general formula (1) and an aldehyde represented by general formula (2) with a hydrogen-donating compound in the presence of an organic iridium compound represented by general formula (3), general formula (4), general formula (5), or general formula (6), and then oxidatively deprotecting the substituent having a 2-hydroxyethyl skeleton on the nitrogen. The hemiaminal ether, imine or enamine may be produced in situ or synthesized independently using the aminoalcohol represented by the above general formula (1) and the aldehyde compound represented by the general formula (2) as raw materials.

[0030] The organic iridium compound used in the present invention functions as a catalyst in this method. The organic iridium compound is represented by the general formula (3): [ka] It is expressed as: In the above general formula (3), Ar is a cyclopentadienyl group in which one or more hydrogen atoms may be substituted with the above-mentioned substituent W.

[0031] Specific examples of Ar include, but are not limited to, an unsubstituted cyclopentadienyl group, a methylcyclopentadienyl group, an ethylcyclopentadienyl group, an isopropylcyclopentadienyl group, a phenylcyclopentadienyl group, a benzylcyclopentadienyl group, a 1,2-dimethylcyclopentadienyl group, a 1,3-dimethylcyclopentadienyl group, a 1,2,3-trimethylcyclopentadienyl group, a 1,2,4-trimethylcyclopentadienyl group, a 1,2,3,4-tetramethylcyclopentadienyl group, a 1,2,3,4,5-pentamethylcyclopentadienyl group (Cp * ), 1,2,3,4,5-pentaphenylcyclopentadienyl group, etc. Among these, 1,2,3,4,5-pentamethylcyclopentadienyl group (Cp * ) and the 1,2,3,4,5-pentaphenylcyclopentadienyl group.

[0032] X is a hydride group or an anionic group. Specific examples of X include, but are not limited to, a hydride group, a hydroxy group, an alkoxy group, a bridged oxo group, a fluorine group, a chlorine group, a bromine group, an iodine group, a tetrafluoroborate group, a tetrahydroborate group, a tetrakispentafluorophenylborate group, a tetrakis[3,5-bis(trifluoromethyl)phenyl]borate group, a hexafluorophosphate group, a hexafluoroantimonate group, a hexachloroantimonate group, a hexafluoroarsenate group, a perchlorate group, an acetoxy group, a benzoyloxy group, a (2,6-dihydroxybenzoyl)oxy group, a (2,5-dihydroxybenzoyl)oxy group, a (3-aminobenzoyl)oxy group, a (2,6-dimethoxybenzoyl)oxy group, a (2,4,6-triisopropylbenzoyl)oxy group,

[0033] Examples of the aryl group include 1-naphthalene carboxylic acid group, 2-naphthalene carboxylic acid group, trifluoroacetoxy group, trifluoromethanesulfonimide group, nitromethyl group, nitroethyl group, toluenesulfonate group, methanesulfonate group, ethanesulfonate group, n-propanesulfonate group, isopropanesulfonate group, n-butanesulfonate group, fluorosulfonate group, fluoromethanesulfonate group, difluoromethanesulfonate group, trifluoromethanesulfonate group, pentafluoroethanesulfonate group, phosphate group, (S)-2,2'-dihydroxy-1,1'-binaphthyl phosphate group, (R)-2,2'-dihydroxy-1,1'-binaphthyl phosphate group, etc. Among these, preferred are hydride group, chlorine group, bromine group, iodine group, tetrafluoroborate group, tetrahydroborate group, and trifluoromethanesulfonate group.

[0034] In addition to the hydride group or anionic group X, Ir may have a neutral molecule that can be coordinated. Specific examples of neutral molecules that can be coordinated to Ir include water, alcohols such as methanol, ethanol, n-propanol, 2-propanol, and 2-methoxyethanol, ethers such as tetrahydrofuran, diethyl ether, diisopropyl ether, cyclopentyl methyl ether, and tert-butyl methyl ether, N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, acetone, chloroform, acetonitrile, benzonitrile, pyridine, trialkylphosphines such as trimethylphosphine, triethylphosphine, and tricyclohexylphosphine, and triarylphosphines such as triphenylphosphine. When such neutral molecules are coordinated, they form a cationic complex, and the anionic group exists as a counter anion.

[0035] R 7 and R 8 are the same or different and each represent a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced with heteroatoms, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to 20 sulfenyl group, a C1 to 20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, and one or more hydrogen atoms of these groups may be substituted with the substituent W.

[0036] R 7 and R 8 may be introduced in a plurality of units, and the numbers of substitutions j and k are the same or different and are integers of 0 to 3. When j is 2 or more, 2 or more R 7may be joined together to form one or more rings, such as a phenanthridine ring, an acridine ring, etc. 7 or R 8 A carbon atom in the quinoline ring to which is not bonded may be replaced by a nitrogen atom to form, for example, a naphthyridine ring, a quinoxaline ring, a cinnoline ring, a quinazoline ring, a phthalazine ring, or the like.

[0037] Ra, Rb and Rc have the same meanings as above, R 7 and R 8 Specific examples of the alkyl group include, but are not limited to, a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, an n-butyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a cyclopentyl group, an n-hexyl group, a cyclohexyl group, a cyclohexylene group, a vinyl group, a propenyl group, a butenyl group, a phenyl group, a toluyl group, a xylyl group, a naphthyl group, a pyridyl group, a furanyl group, a thienyl group, a pyrrolidyl group, a piperidyl group, a methoxy group, an ethoxy group, a propoxy group, a benzyloxy group, an acetyl group, a propionyl group, a cyclohexanecarbonyl group, a benzoyl group, a methoxycarbonyl group, an ethoxycarbonyl group, an acetyloxy group, a benzoyloxy group, a hydroxyl group,

[0038] methylamino group, ethylamino group, n-propylamino group, isopropylamino group, dimethylamino group, diethylamino group, di-n-propylamino group, diisopropylamino group, carbamoyl group, N-methylcarbamoyl group, N,N-dimethylcarbamoyl group, N-acetylamino group, N-methyl-N-acetylamino group, N-benzoylamino group, N-methyl-N-benzoylamino group, nitro group, cyano group, diphenylphosphino group, dicyclohexylphosphino group, cyclopropylphosphino group, cyclobutylphosphino group, cyclopentylphosphino group, cyclohexylphosphino group, methanesulfenyl group, ethanesulfenyl group, benzenesulfonyl group, p-toluenesulfonyl group, trifluoromethanesulfonyl group, sulfo group, mercapto group, methylsilyl group, dimethylsilyl group, trimethylsilyl group,

[0039] Examples of the fluorine group include a bromine group, a chlorine group, an iodine group, and a trifluoromethyl group. 7 and R 8 is preferably a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a phenyl group, a methoxy group, an ethoxy group, a propoxy group, a benzyloxy group, a hydroxyl group, a dimethylamino group, a diethylamino group, a nitro group, a cyano group, a fluorine group, or a trifluoromethyl group, and particularly preferably a hydrogen atom, a methyl group, an isopropyl group, a methoxy group, an ethoxy group, a hydroxyl group, a dimethylamino group, a nitro group, or a trifluoromethyl group.

[0040] The organic iridium compound used in the present invention is represented by the general formula (4): [ka] It is expressed as: In the formula, Ar, X and R 7 has the same meaning as above.

[0041] R 7 may be introduced in a plurality of units, and the number of substitutions l is an integer of 0 to 4. When l is 2 or more, 2 or more R7 may be joined together to form one or more rings, such as a quinoline ring, an isoquinoline ring, etc. 7 A carbon atom in the pyridine ring to which is not bonded may be replaced by a nitrogen atom to form, for example, a pyridazine ring, a pyrazine ring, a pyrimidine ring, a triazine ring, or the like.

[0042] R 9 represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced with heteroatoms, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 sulfenyl group, a C1 to C20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, and one or more hydrogen atoms of these groups may be substituted by the substituent W.

[0043] Ra, Rb and Rc have the same meanings as above, R 9 Specific examples of the aryl group include, but are not limited to, a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, an n-butyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a cyclopentyl group, an n-hexyl group, a cyclohexyl group, a cyclohexylene group, a vinyl group, a propenyl group, a butenyl group, a phenyl group, a toluyl group, a xylyl group, a diethylphenyl group, a diisopropylphenyl group, a 4-methoxyphenyl group, a 4-dimethylaminophenyl group, a 4-hydroxyphenyl group, a naphthyl group, a pyridyl group, a furanyl group, a thienyl group, a pyrrolidyl group, a piperidyl group, a methoxy group, an ethoxy group, a propoxy group, a benzyloxy group, an acetyl group, a propionyl group, a cyclohexanecarbonyl group, a benzoyl group, a methoxycarbonyl group, an ethoxycarbonyl group, an acetyloxy group, a benzoyloxy group, a hydroxyl group,

[0044] Methylamino group, ethylamino group, n-propylamino group, isopropylamino group, dimethylamino group, diethylamino group, di-n-propylamino group, diisopropylamino group, carbamoyl group, N-methylcarbamoyl group, N,N-dimethylcarbamoyl group, N-acetylamino group, N-methyl-N-acetylamino group, N-benzoylamino group, N-methyl-N-benzoylamino group, nitro group, cyano group, diphenylphosphino group, dicyclohexylphosphino group, Examples of such groups include a cyclopropylphosphino group, a cyclobutylphosphino group, a cyclopentylphosphino group, a cyclohexylphosphino group, a methanesulfenyl group, an ethanesulfenyl group, a methanesulfonyl group, an ethanesulfonyl group, a benzenesulfonyl group, a p-toluenesulfonyl group, a trifluoromethanesulfonyl group, a sulfo group, a mercapto group, a methylsilyl group, a dimethylsilyl group, a trimethylsilyl group, a fluorine group, a bromine group, a chlorine group, an iodine group, and a trifluoromethyl group.

[0045] Preferred are a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a phenyl group, a toluyl group, a xylyl group, a diisopropylphenyl group, a 4-methoxyphenyl group, a 4-dimethylaminophenyl group, a 4-hydroxyphenyl group, a 4-trifluoromethylphenyl group, a 4-cyanophenyl group, a 4-fluorophenyl group, and a 4-nitrophenyl group, and particularly preferred are a hydrogen atom, a methyl group, a phenyl group, a p-toluyl group, a 2,6-xylyl group, a 2,6-diisopropylphenyl group, a 4-methoxyphenyl group, a 4-dimethylaminophenyl group, a 4-hydroxyphenyl group, a 4-trifluoromethylphenyl group, and a 4-nitrophenyl group.

[0046] The organic iridium compound used in the present invention is represented by the general formula (5): [ka] It is expressed as: In the formula, Ar, X, R 7 , l has the same meaning as above.

[0047] R 7 may be introduced in plural, and when the number of substitutions l is 2 or more, 2 or more R 7 may be joined together to form one or more rings, such as a quinoline ring, an isoquinoline ring, etc. 7 A carbon atom in the pyridine ring to which is not bonded may be replaced by a nitrogen atom to form, for example, a pyridazine ring, a pyrazine ring, a pyrimidine ring, a triazine ring, or the like.

[0048] R 10 and R 11 are the same or different and each represent a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced with heteroatoms, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to 20 sulfenyl group, a C1 to 20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, and one or more hydrogen atoms of these groups may be substituted with the substituent W.

[0049] Ra, Rb and Rc have the same meanings as above, R 10 and R 11 Specific examples of the alkyl group include, but are not limited to, a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, an n-butyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a cyclopentyl group, an n-hexyl group, a cyclohexyl group, a 2,6-dimethylcyclohexyl group, a 2,2,6,6-tetramethylcyclohexyl group, a cyclohexylene group, a vinyl group, a propenyl group, a butenyl group, a phenyl group, a toluyl group, a xylyl group, a mesityl group,

[0050] pentamethylphenyl group, 4-methoxyphenyl group, 3,5-dimethoxyphenyl group, 2,6-dimethoxyphenyl group, 4-dimethylaminophenyl group, 4-hydroxyphenyl group, naphthyl group, anthracenyl group, fluorenyl group, phenalenyl group, phenanthrenyl group, indenyl group, pyridyl group, furanyl group, thienyl group, pyrrolidyl group, piperidyl group, methoxy group, ethoxy group, propoxy group, benzyloxy group, acetyl group, propionyl group, cyclohexanecarbonyl group, benzoyl group, methoxycarbonyl group, ethoxycarbonyl group, acetyloxy group, benzoyloxy group, hydroxyl group, methylamino group, ethylamino group, n-propylamino group, isopropylamino group, dimethylamino group, diethylamino group, di-n-propylamino group, diisopropylamino group,

[0051] carbamoyl group, N-methylcarbamoyl group, N,N-dimethylcarbamoyl group, N-acetylamino group, N-methyl-N-acetylamino group, N-benzoylamino group, N-methyl-N-benzoylamino group, nitro group, cyano group, diphenylphosphino group, dicyclohexylphosphino group, cyclopropylphosphino group, cyclobutylphosphino group, cyclopentylphosphino group, cyclohexylphosphino group, methanesulfenyl group, ethanesulfenyl group, benzenesulfonyl group, p-toluenesulfonyl group, trifluoromethanesulfonyl group, sulfo group, mercapto group, methylsilyl group, dimethylsilyl group, trimethylsilyl group,

[0052] Examples of the fluorine group, bromine group, chlorine group, iodine group, and trifluoromethyl group are mentioned. Preferred are hydrogen atom, methyl group, ethyl group, isopropyl group, isobutyl group, tert-butyl group, cyclohexyl group, phenyl group, toluyl group, xylyl group, mesityl group, pentamethylphenyl group, 4-methoxyphenyl group, 3,5-dimethoxyphenyl group, 2,6-dimethoxyphenyl group, 4-dimethylaminophenyl group, 4-hydroxyphenyl group, naphthyl group, anthracenyl group, fluorenyl group, phenalenyl group, phenanthrenyl group, and indenyl group, and particularly preferred are hydrogen atom, methyl group, isopropyl group, phenyl group, p-toluyl group, 3,5-xylyl group, 2,6-xylyl group, 2,4,6-mesityl group, and pentamethylphenyl group. R 10 and R 11 may be combined with each other to form a ring.

[0053] R 12 R is a C1 to C20 sulfonyl group, -C(=O)-Ra or -C(=O)-NRaRb, and one or more hydrogen atoms of these groups may be substituted with the substituent W. 12 Specific examples of the sulfonyl group include, but are not limited to, a methanesulfonyl group (Ms), an ethanesulfonyl group (Es), an n-propylsulfonyl group, an isopropylsulfonyl group, an n-butylsulfonyl group, an isobutylsulfonyl group, an n-pentylsulfonyl group, a cyclopentylsulfonyl group, a 1-octanesulfonyl group, a 1-hexadecanesulfonyl group, an o-toluenesulfonyl group, an m-toluenesulfonyl group, a p-toluenesulfonyl group (Ts), a benzenesulfonyl group, a 2,6-dimethylbenzenesulfonyl group, a 3,5-dimethylbenzenesulfonyl group, a 2,4,6-trimethylbenzenesulfonyl group, a 2,4,6-triisopropylbenzenesulfonyl group,

[0054] 4-cyanobenzenesulfonyl group, 2-nitrobenzenesulfonyl group, 3-nitrobenzenesulfonyl group, 4-nitrobenzenesulfonyl group, 2,4-dinitrobenzenesulfonyl group, 2-(trifluoromethyl)benzenesulfonyl group, 4-(trifluoromethyl)benzenesulfonyl group, 3,5-bis(trifluoromethyl)benzenesulfonyl group, 4-chlorobenzenesulfonyl group, 2,4-dichlorobenzenesulfonyl group, 4-fluorobenzenesulfonyl group, 3,4,5-trifluorobenzenesulfonyl group, 2,3,4,5,6-pentafluorobenzenesulfonyl group, 4-methoxybenzenesulfonyl group, (+)-10-camphorsulfonyl group, (-)-10-camphorsulfonyl group, pyridine-3-sulfonyl group, trichloromethanesulfonyl group, trifluoromethanesulfonyl group, 2,2,2-trifluoroethanesulfonyl group, 4-hydroxybenzenesulfonyl group, 4-biphenylbenzenesulfonyl group, benzylsulfonyl group (-SO2Bn),

[0055] Acetyl group, propionyl group, isopropylcarbonyl group, tert-butylcarbonyl group, benzoyl group, trifluoroacetyl group, trichloroacetyl group, pentafluoropropionyl group, 3,3,3-trifluoropropionyl group, methoxycarbonyl group, ethoxycarbonyl group, isopropyloxycarbonyl group, tert-butoxycarbonyl group (Boc), phenoxycarbonyl group, carbamoyl group, N-methylcarbamoyl group, N-ethylcarbamoyl group, N-isopropylcarbamoyl group, N-tert-butylcarbonyl group, N-trifluoromethylcarbamoyl group, N-phenylcarbamoyl group, N-(4-fluorophenyl) Examples of such an alkyl group include an N-(4-phenyl)carbamoyl group, an N-(4-cyanophenyl)carbamoyl group, an N-(4-nitrophenyl)carbamoyl group, an N-(4-trifluoromethylphenyl)carbamoyl group, an N-(3,5-bis(trifluoromethyl)phenyl)carbamoyl group, an N-(3,5-difluorophenyl)carbamoyl group, and an N-(3,4,5-trifluorophenyl)carbamoyl group. Preferred are a methanesulfonyl group, an ethanesulfonyl group, a p-toluenesulfonyl group, a benzenesulfonyl group, a benzylsulfonyl group, an acetyl group, a trifluoroacetyl group, and an N-phenylcarbamoyl group, and particularly preferred is a methanesulfonyl group.

[0056] Furthermore, the organic iridium compound used in the present invention is represented by the general formula (6): [ka] It can be expressed as: In the formula, Ar and X have the same meanings as above.

[0057] A is a saturated or unsaturated nitrogen-containing heterocyclic carbene containing at least two nitrogen atoms, in which one or more hydrogen atoms may be substituted with the substituent W. The heterocycle constituting A is composed of at least a heterocycle having a carbene structure. The heterocycle having a carbene structure contains two nitrogen atoms and one or more carbon atoms as ring members, and is composed so that one carbon atom is sandwiched between the two nitrogen atoms and the carbon atom forms a carbene structure. This allows A to be coordinated to Ir as a carbene ligand. A may be a monocyclic group or a polycyclic group. When A is a monocyclic group, A is a heteromonocyclic group having only the above-mentioned heterocycle having a carbene structure as a ring structure. On the other hand, when A is a polycyclic group, A contains one or more rings in addition to the heterocycle having the above-mentioned carbene structure. In this case, each ring can be bonded to each other by a spiro bond or condensation, or formed by bridging other rings. Preferably, each ring is bonded to each other by condensation.

[0058] The heterocycle containing the carbene structure can be saturated or unsaturated. The heterocycle having a carbene structure is composed of two nitrogen atoms and one or more carbon atoms, and may further contain one or more heteroatoms as ring members, such as nitrogen, oxygen and sulfur atoms. Examples of the heterocycle having a carbene structure include, but are not limited to, carbene rings such as an imidazole ring, an imidazoline ring, an imidazolidine ring, a 1,2,4-triazole ring, a tetrazole ring, an oxazoline ring, an oxazole ring, an oxazolidine ring, a thiazoline ring, a thiazole ring, a thiazolidine ring, etc. In particular, it is preferable that A is a monocyclic or polycyclic carbene containing an imidazole ring, an imidazoline ring, or an imidazolidine ring as the heterocycle having a carbene structure.

[0059] In addition, the rings in A other than the heterocycle having a carbene structure can each be saturated or unsaturated. In addition, the rings other than the heterocycle having a carbene structure in A may be either hydrocarbon rings or heterocycles. When the ring is a heterocycle, the ring contains one or more heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom. The number of ring members in each ring constituting A is not limited to this, but is, for example, 4 to 8, and preferably 4 to 6. In particular, the number of ring members in the heterocycle having a carbene structure is preferably 4 to 6, and more preferably 5.

[0060] Specific examples of A include carbene rings such as monocyclic heteroaromatic rings such as an imidazole ring, a 1,2,4-triazole ring, and a tetrazole ring; monocyclic non-aromatic heterocyclic rings such as an imidazoline ring and an imidazolidine ring; and polycyclic heteroaromatic rings such as a benzimidazole ring, a purine ring, and a pteridine ring. Among the above, from the viewpoints of reactivity and catalytic activity, an imidazole ring or a carbene ring of an imidazoline ring is preferred, and a carbene ring of an imidazole ring is more preferred.

[0061] R 13 , R 14 , R 15 , R 16 and R 17 are the same or different and each represent a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced with heteroatoms, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to 20 sulfenyl group, a C1 to 20 sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, and one or more hydrogen atoms of these groups may be substituted with the substituent W.

[0062] Ra, Rb and Rc have the same meanings as above, R13 , R 14 , R 15 , R 16 and R 17 Specific examples of the aryl group include, but are not limited to, a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, an n-butyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a cyclopentyl group, an n-hexyl group, a cyclohexyl group, a 2,6-dimethylcyclohexyl group, a 2,2,6,6-tetramethylcyclohexyl group, a cyclohexylene group, a vinyl group, a propenyl group, a butenyl group, a phenyl group, a toluyl group, a xylyl group, a mesityl group, a pentamethylphenyl group, a 4-methoxyphenyl group, a phenyl group, a 3,5-dimethoxyphenyl group, a 2,6-dimethoxyphenyl group, a 4-dimethylaminophenyl group, a 4-hydroxyphenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, a phenalenyl group, a phenanthrenyl group, an indenyl group, a pyridyl group, a furanyl group, a thienyl group, a pyrrolidyl group, a piperidyl group, a methoxy group, an ethoxy group, a propoxy group, a benzyloxy group, an acetyl group, a propionyl group, a cyclohexanecarbonyl group, a benzoyl group, a methoxycarbonyl group, an ethoxycarbonyl group, an acetyloxy group, a benzoyloxy group,

[0063] Hydroxyl group, methylamino group, ethylamino group, n-propylamino group, isopropylamino group, dimethylamino group, diethylamino group, di-n-propylamino group, diisopropylamino group, carbamoyl group, N-methylcarbamoyl group, N,N-dimethylcarbamoyl group, N-acetylamino group, N-methyl-N-acetylamino group, N-benzoylamino group, N-methyl-N-benzoylamino group, nitro group, cyano group, diphenylphosphino group, dicyclohexylphosphine group, Examples of the alkyl group include a cyclophenyl group, a cyclopropylphosphino group, a cyclobutylphosphino group, a cyclopentylphosphino group, a cyclohexylphosphino group, a methanesulfenyl group, an ethanesulfonyl group, a benzenesulfonyl group, a p-toluenesulfonyl group, a trifluoromethanesulfonyl group, a sulfo group, a mercapto group, a methylsilyl group, a dimethylsilyl group, a trimethylsilyl group, a fluorine group, a bromine group, a chlorine group, an iodine group, and a trifluoromethyl group.

[0064] Preferred are a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, an isobutyl group, a tert-butyl group, a cyclohexyl group, a phenyl group, a toluyl group, a xylyl group, a mesityl group, a pentamethylphenyl group, a 4-methoxyphenyl group, a 3,5-dimethoxyphenyl group, a 2,6-dimethoxyphenyl group, a 4-dimethylaminophenyl group, a 4-hydroxyphenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, a phenalenyl group, a phenanthrenyl group, and an indenyl group, and particularly preferred are a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a phenyl group, a p-toluyl group, a 3,5-xylyl group, a 2,6-xylyl group, a 2,4,6-mesityl group, and a pentamethylphenyl group.

[0065] R 18 R is a C1 to C20 sulfonyl group, -C(=O)-Ra, -C(=O)-ORa, -C(=O)-NRaRb, -C(=S)-NRaRb, a C1 to C20 fluoroalkyl group, or an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, and one or more hydrogen atoms of these groups may be replaced by the substituent W.18 Specific examples of the sulfonyl group include, but are not limited to, a methanesulfonyl group (Ms), an ethanesulfonyl group (Es), an n-propylsulfonyl group, an isopropylsulfonyl group, an n-butylsulfonyl group, an isobutylsulfonyl group, an n-pentylsulfonyl group, a cyclopentylsulfonyl group, a 1-octanesulfonyl group, a 1-hexadecanesulfonyl group, an o-toluenesulfonyl group, an m-toluenesulfonyl group, a p-toluenesulfonyl group (Ts), a benzenesulfonyl group, a 2,6-dimethylbenzenesulfonyl group, a 3,5-dimethylbenzenesulfonyl group, a 2,4,6-trimethylbenzenesulfonyl group, a 2,4,6-triisopropylbenzenesulfonyl group, a 4-cyanobenzenesulfonyl group, a 2-nitrobenzenesulfonyl group, a 3-nitrobenzenesulfonyl group, a 4-nitrobenzenesulfonyl group, a 2,4-diphenyl ... Nitrobenzenesulfonyl group, 2-(trifluoromethyl)benzenesulfonyl group, 4-(trifluoromethyl)benzenesulfonyl group, 3,5-bis(trifluoromethyl)benzenesulfonyl group, 4-chlorobenzenesulfonyl group, 2,4-dichlorobenzenesulfonyl group, 4-fluorobenzenesulfonyl group, 3,4,5-trifluorobenzenesulfonyl group, 2,3,4,5,6-pentafluorobenzenesulfonyl group, 4-methoxybenzenesulfonyl group, (+)-10-camphorsulfonyl group, (-)-10-camphorsulfonyl group, pyridine-3-sulfonyl group, trichloromethanesulfonyl group, trifluoromethanesulfonyl group, 2,2,2-trifluoroethanesulfonyl group, 4-hydroxybenzenesulfonyl group, 4-biphenylbenzenesulfonyl group, benzylsulfonyl group (-SO2Bn),

[0066] Acetyl group, propionyl group, isopropylcarbonyl group, tert-butylcarbonyl group, benzoyl group, trifluoroacetyl group, trichloroacetyl group, pentafluoropropionyl group, 3,3,3-trifluoropropionyl group, methoxycarbonyl group, ethoxycarbonyl group, isopropyloxycarbonyl group, tert-butoxycarbonyl group (Boc), phenoxycarbonyl group, carbamoyl group, N-methylcarbamoyl group, N-ethylcarbamoyl group, N-isopropylcarbamoyl group, N-tert-butylcarbonyl group, N-to trifluoromethylcarbamoyl group, N-phenylcarbamoyl group, N-(4-fluorophenyl)carbamoyl group, N-(4-cyanophenyl)carbamoyl group, N-(4-nitrophenyl)carbamoyl group, N-(4-trifluoromethylphenyl)carbamoyl group, N-(3,5-bis(trifluoromethyl)phenyl)carbamoyl group, N-(3,5-difluorophenyl)carbamoyl group, N-(3,4,5-trifluorophenyl)carbamoyl group, thiocarbamoyl group, N-methylthiocarbamoyl group, N-phenylthiocarbamoyl group,

[0067] Examples of such groups include a trifluoromethyl group, a pentafluoroethyl group, a phenyl group, a 4-nitrophenyl group, a 4-cyanophenyl group, a 4-fluorophenyl group, a 3,5-difluorophenyl group, a 3,4,5-trifluorophenyl group, a 4-(trifluoromethyl)phenyl group, a 3,5-bis(trifluoromethyl)phenyl group, and a pentafluorophenyl group. Preferred are a methanesulfonyl group, an ethanesulfonyl group, a p-toluenesulfonyl group, a benzenesulfonyl group, a benzylsulfonyl group, an acetyl group, a trifluoroacetyl group, and an N-phenylcarbamoyl group.

[0068] Among the above-mentioned substituents, R 14 , R 15 , R 16 , R 17 and R 18Two or more groups selected from the group consisting of may be joined together to form one or more rings. The ring thus formed is not particularly limited, but examples thereof include a cycloalkane ring, a cycloalkene ring, a cycloalkyne ring, an aromatic ring, a hetero ring, a cyclic ketone, a lactone ring, a lactam ring, a carbamate ring, a urea ring, and a thiourea ring. In addition, one or more hydrogen atoms of these groups may be substituted with the substituent W. The number of ring members of these rings is not particularly limited, but may be, for example, 3 to 20, preferably 3 to 12, and more preferably 4 to 8.

[0069] Specific examples of such rings include, but are not limited to, a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a cyclopentanone ring, a cyclohexanone ring, a cycloheptanone ring, a cyclooctanone ring, a benzene ring, a pyran ring, a furan ring, a pyrrole ring, an imidazoline ring, an imidazole ring, an imidazolidine ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyrrolidine ring, a piperidine ring, a piperazine ring, a morpholine ring, a β-lactam, a γ-lactam, a δ-lactam, a 2-oxazolidinone ring, a 2-imidanolidinone ring, a tetrahydro-2-pyrimidinone ring, a 2-imidazolidinone ring, a tetrahydro-2-pyrimidinethione ring, and the like.

[0070] In particular, R 16 and / or R 17 and R 18 That is, R 16 and R 18 , R 17 and R 18 or R 16 and R 17 and R 18 are preferably taken together to form a ring. In such a case, the ring formed is preferably a lactam ring, a heterocycle, a carbamate ring, a urea ring, or a thiourea ring, and more preferably a γ-lactam, a 2-oxazolidinone ring, a 2-imidazolidinone ring, a tetrahydro-2-pyrimidinone ring, a 2-imidazolidinone ring, or a tetrahydro-2-pyrimidinethione ring.

[0071] In the present invention, a primary or secondary amine compound can also be produced by reacting an aminoalcohol represented by the above-mentioned general formula (1) and an aldehyde compound represented by the general formula (2) with a hydrogen-donating compound in the presence of an organic iridium compound represented by the below-mentioned general formula (7) and an organic compound represented by the general formula (8), general formula (9), general formula (10) or general formula (11), and then oxidatively deprotecting the substituent having a 2-hydroxyethyl skeleton on the nitrogen.

[0072] Furthermore, it is also possible to produce a primary or secondary amine compound by reacting a hemiaminal ether, imine or enamine prepared from an aminoalcohol represented by the above-mentioned general formula (1) and an aldehyde compound represented by the general formula (2) with a hydrogen donor compound in the presence of an organic iridium compound represented by the below-mentioned general formula (7) and an organic compound represented by the general formula (8), general formula (9), general formula (10) or general formula (11), and then oxidatively deprotecting the substituent having a 2-hydroxyethyl skeleton on the nitrogen. That is, an organic iridium compound represented by general formula (7) and an organic compound represented by general formula (8), general formula (9), general formula (10) or general formula (11) form an organic iridium compound corresponding to general formula (3), general formula (4), general formula (5) or general formula (6), respectively, in the reaction system, and function as a catalyst.

[0073] The organic iridium compound used in the present invention is represented by the general formula (7) JPEG0007659382000037.jpg2046, where Ar and X have the same meanings as above. The organic compound used in the present invention is represented by the general formula (8): [ka] General formula (9), [ka] General formula (10), [ka] Or general formula (11) [ka] It is expressed as:

[0074] In these formulas, R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , j, k, and l have the same meanings as above. A' is a saturated or unsaturated nitrogen-containing heterocyclic carbene precursor containing at least two nitrogen atoms, one or more hydrogen atoms of which may be substituted by the substituent W, and becomes the above-mentioned saturated or unsaturated nitrogen-containing heterocyclic carbene A by eliminating a proton on the carbon atom sandwiched between the two nitrogen atoms. That is, A' has the same meaning as that obtained by replacing the carbene in the above-mentioned A with a carbene precursor.

[0075] Y is an anionic group, and specific examples thereof include, but are not limited to, a fluorine group, a chlorine group, a bromine group, an iodine group, a tetrafluoroborate group, a tetrahydroborate group, a tetrakispentafluorophenylborate group, a tetrakis[3,5-bis(trifluoromethyl)phenyl]borate group, a hexafluorophosphate group, a hexafluoroantimonate group, a hexachloroantimonate group, a hexafluoroarsenate group, a perchlorate group, an acetoxy group, a benzoyloxy group, a (2,6-dihydroxybenzoyl)oxy group, a (2,5-dihydroxybenzoyl)oxy group, a (3-aminobenzoyl)oxy group, a (2,6-dimethoxybenzoyl)oxy group, a (2,4,6- triisopropylbenzoyl)oxy group, 1-naphthalene carboxylic acid group, 2-naphthalene carboxylic acid group, trifluoroacetoxy group, trifluoromethanesulfonimide group, toluenesulfonate group, methanesulfonate group, ethanesulfonate group, n-propanesulfonate group, isopropanesulfonate group, n-butanesulfonate group, fluorosulfonate group, fluoromethanesulfonate group, difluoromethanesulfonate group, trifluoromethanesulfonate group, pentafluoroethanesulfonate group, phosphate group, (S)-2,2'-dihydroxy-1,1'-binaphthyl phosphate group, (R)-2,2'-dihydroxy-1,1'-binaphthyl phosphate group, etc. Among these, preferred are chlorine group, bromine group, iodine group, tetrafluoroborate group, tetrahydroborate group, p-toluenesulfonate group, methanesulfonate group, or trifluoromethanesulfonate group.

[0076] The hydrogen-donating compound in the present invention means a compound capable of donating hydrogen by thermal action or catalytic action, and the type of such a hydrogen-donating compound is not particularly limited. Suitable hydrogen-donating compounds include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, isobutyl alcohol, 1-pentanol, cyclopentyl alcohol, 1-hexanol, cyclohexyl alcohol, benzyl alcohol, formic acid, sodium formate, potassium formate, lithium formate, and ammonium formate, and can be used alone or in combination. In terms of reactivity and economy, formic acid, formate salts, methanol, ethanol, and 2-propanol are preferred.

[0077] The amount of the hydrogen donating compound used can be 1 to 30 equivalents relative to the aldehyde compound, but is preferably 1 to 10 equivalents in terms of reactivity and economy. When a formate such as sodium formate, potassium formate, lithium formate, or ammonium formate is used as the hydrogen donating compound, a phase transfer catalyst may be added as necessary to carry out the reaction. Any salt having a long-chain alkyl ammonium cation may be used as the phase transfer catalyst, but tetrabutylammonium salt is preferred in terms of reactivity and economy. In many cases, the addition of a phase transfer catalyst has the effect of improving the reaction rate. The amount of the phase transfer catalyst added is usually in the range of 0.001 to 10 molar equivalents relative to the aldehyde compound, but is preferably 0.01 to 0.1 molar equivalents in terms of reactivity and economy.

[0078] The amount of the amino alcohol used is usually 1 to 30 equivalents relative to the aldehyde compound, but from the standpoint of reactivity and economic efficiency, it is preferably 1 to 10 equivalents. It can also be used as an amino alcohol salt.

[0079] The amount of the organic iridium compound used, expressed as the molar ratio of the aldehyde compound to the organic iridium compound, S / C (substrate / catalyst molar ratio), varies greatly depending on the structure of the aldehyde compound, the type and concentration of the organic iridium compound, the reaction temperature, the type of hydrogen-donating compound, etc., but can be in the range of S / C = 10 to 10,000,000, preferably in the range of S / C = 100 to 1,000,000.

[0080] In the reaction of the first step of the present invention, that is, the reaction between an amino alcohol and an aldehyde compound, or the reaction between a hemiaminal ether, an imine, or an enamine, a suitable reaction solvent can be used in consideration of the physical and chemical properties of the substrate, the product, the organic iridium compound, and the hydrogen donor compound. Protic solvents, aprotic solvents, ionic liquids, water, and buffer solutions can be used alone or in combination. In terms of reactivity and economy, water, methanol, ethanol, 2-propanol, ethylene glycol, ethyl acetate, propyl acetate, butyl acetate, tetrahydrofuran, tert-butyl methyl ether, diisopropyl ether, ethylene glycol dimethyl ether, acetonitrile, toluene, chloroform, and methylene chloride are preferred.

[0081] The reaction temperature in the first step is preferably about −20° C. to 100° C., taking into consideration the solubility and reactivity of the substrate and product, and economic efficiency, and is more preferably 20° C. to 80° C. The reaction time varies depending on reaction conditions such as S / C, substrate concentration, and temperature, but the reaction is completed within a few minutes to 100 hours.

[0082] In the second step of the present invention, a substituent having a 2-hydroxyethyl skeleton on the nitrogen atom, i.e., the reaction product of the first step, is represented by the following general formula (A): [ka] In the formula, R 2 , R 3 , R 4 , R 5The oxidative deprotection reaction of the site represented by (wherein n has the same meaning as in general formula (1)) is achieved by oxidative cleavage of the carbon-carbon bond of the 2-amino-1-ethanol skeleton, followed by hydrolysis. As an oxidizing agent for driving this reaction, an oxidizing agent used in the oxidative cleavage of 1,2-diols can be used, and is not particularly limited to the type, but for example, periodic acid, periodate such as sodium periodate, potassium periodate, and ammonium periodate, lead tetraacetate, hypervalent iodine compounds such as (diacetoxyiodo)benzene and Dess-Martin periodinane, sodium hypochlorite, etc. can be used alone or in combination. In consideration of reactivity and economic efficiency, periodic acid, periodate, lead tetraacetate, and Dess-Martin periodinane are preferred.

[0083] The amount of the oxidizing agent used may be 1 to 30 equivalents relative to the aldehyde compound, but from the standpoint of reactivity and economic efficiency, it is preferably 1 to 10 equivalents.

[0084] In the second step, a reaction solvent can be appropriately used in consideration of the physical and chemical properties of the substrate, product, and oxidizing agent. It is preferable to use a solvent according to the properties of the oxidizing agent used, and protic solvents, aprotic solvents, ionic liquids, water, and buffer solutions can be used alone or in combination.

[0085] The reaction temperature in the second step is also appropriately selected in consideration of the physical and chemical properties and reactivity of the substrate, product and oxidizing agent, and economic efficiency. It is particularly preferable to select the temperature according to the properties of the oxidizing agent used. The reaction can usually be carried out at about -78°C to 100°C. The reaction time varies depending on reaction conditions such as the properties and amount of the oxidizing agent, the substrate concentration and temperature, but the reaction is completed within a few minutes to 100 hours.

[0086] The produced primary or secondary amine compound can be purified by known methods such as acid-base extraction, column chromatography, distillation, salification, recrystallization, etc., or by a suitable combination of these methods. The reaction format of the above reaction is not particularly limited, and the reaction can be carried out in any of a batch system, a continuous system, and a flow reactor. EXAMPLES

[0087] The present invention will be described in more detail below with reference to examples. Of course, the present invention is not limited to the following examples. In the following examples, the substrates, catalysts, reactants, solvents, etc. used in the reactions were purchased reagents unless otherwise specified. NMR was measured using a JNM-ECX400P (400 MHz, JEOL). 1 For H-NMR, tetramethylsilane (TMS) was used as the internal standard, and its signal was set to δ=0 (δ is the chemical shift). GC was performed using a 7890B (Agilent Technologies) with an HP-5 column (30 m × 0.32 mm × 0.25 μm, Agilent Technologies). Cp * IrCl (N-(4-dimethylaminophenyl)-4-dimethylaminopyridine-2-carboxylic acid amidate) (Ir-PA), Cp * IrCl(8-quinolinolate) (Ir-QN1) and Cp * IrCl(4-dimethylamino-8-quinolinolate) (Ir-QN2) was used as a purchased reagent. Cp * IrCl (N-((2,4,6-mesityl)(2-pyridyl)methyl)methanesulfonamidate) (Ir-PSA) and Cp * IrCl (5-((3,4,5-triethyl-4-imidazolin-2-ylidene-1-yl)methyl)-1-pyrrolidinate-2-one) (Ir-CA) was synthesized with reference to the methods described in Japanese Patent Nos. 6227889 and 6254811, respectively.

[0088] [Comparative Example 1] Synthesis of 4-methoxybenzylamine using sodium cyanoborohydride Into an argon-purged Schlenk flask were charged para-anisaldehyde (0.136 g, 1 mmol), ammonium acetate (1.93 g, 25 mmol), 28% aqueous ammonia (8 mL), and ethanol (20 mL). Sodium cyanoborohydride (0.186 g, 3 mmol) was added, and the reaction solution was stirred at reflux temperature for 19 hours. Approximately 5% aqueous sodium hydroxide was added to the reaction solution, and the mixture was stirred and extracted three times with methylene chloride. The methylene chloride phases were combined, washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain the product. NMR and GC analyses showed that only 46% of the desired 4-methoxybenzylamine was produced, with the remainder being dimers and trimers.

[0089] [Comparative Example 2] Synthesis of N-methyl-4-methoxybenzylamine using sodium triacetoxyborohydride Into an argon-purged Schlenk flask were placed para-anisaldehyde (0.681 g, 5 mmol) and tetrahydrofuran (25 mL). Sodium triacetoxyborohydride (1.59 g, 7.5 mmol) was added, and the reaction solution was stirred at room temperature for 20 hours. Approximately 5% aqueous sodium hydroxide was added to the reaction solution, which was then stirred and extracted twice with diethyl ether. The diethyl ether phases were combined, dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain the product. NMR and GC analyses showed that only 64% of the desired N-methyl-4-methoxybenzylamine was produced, with the remainder being a dimer.

[0090] [Comparative Example 3] Catalytic reductive amination reaction of para-anisaldehyde with an ammonia equivalent Ir-PA (1.29 mg, 2 μmol) and ammonium formate (3.78 g, 60 mmol) were placed in a Schlenk flask and argon purged. Methanol (20 mL), para-anisaldehyde (2.73 g, 20 mmol), and acetic acid (2.3 mL, 40 mmol) were added. The reaction solution was vigorously stirred at 40°C for 18 hours. The reaction solution was neutralized by adding an aqueous sodium hydroxide solution and extracted with diethyl ether. The diethyl ether phase was washed with water and then with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain the product. NMR and GC analyses showed that no 4-methoxybenzylamine was produced, but dimers and trimers were produced.

[0091] [Example 1] Synthesis of N-(2-hydroxyethyl)-4-methoxybenzylamine Ir-PA (0.53 mg, 0.823 μmol) was placed in a Schlenk flask and argon purged. Methanol (41 mL), para-anisaldehyde (5.60 g, 41.1 mmol), 2-aminoethanol (3.02 g, 49.4 mmol), and formic acid (5.68 g, 123 mmol) were added. The reaction solution was vigorously stirred at 40°C for 24 hours. The reaction solution was concentrated under reduced pressure to remove the methanol, and then neutralized by adding about 10% aqueous sodium hydroxide solution and extracted three times with ethyl acetate. The ethyl acetate phases were combined, washed with water and then with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was removed by distillation to obtain 6.88 g of the target product. NMR and GC analyses showed that 99% N-(2-hydroxyethyl)-4-methoxybenzylamine was produced in a yield of 92%. 1 H NMR (CDCl3,400MHz): δ2.0(br,1H),2.79(t,2H,J=5.0Hz),3.64(t,2H,J=5.0Hz),3.74(s,2H),3.80(s,3H),6.87(m,2H),7.23(m,2H). 13 C{ 1 H}NMR(CDCl3,100MHz):δ50.4,52.9,55.3,113.8,129.3,132.2,158.7.

[0092] [Example 2] Synthesis of 4-methoxybenzylamine N-(2-hydroxyethyl)-4-methoxybenzylamine (5.71 g, 31.5 mmol) was charged into a four-neck flask purged with argon. 95 mL of methanol, 95 mL of water, 32 mL of 40% aqueous methylamine solution, and sodium periodate (17.5 g, 81.9 mmol) were added and vigorously stirred at room temperature for 18 hours. Insoluble matter was filtered off and washed with methanol, and then the methanol was distilled off under reduced pressure. 5% aqueous sodium hydroxide solution was added, and the mixture was extracted three times with ethyl acetate. The ethyl acetate phases were combined, washed with water and then with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain 3.75 g of the target product. NMR analysis showed that 4-methoxybenzylamine was produced in a yield of 87%. 1 H NMR (CDCl3,400MHz): δ1.5(br,2H),3.80(s,2H),3.80(s,3H),6.87(m,2H),7.23(m,2H). 13 C{ 1 H}NMR(CDCl3,100MHz):δ45.9,55.3,113.9,128.2,135.6,158.4.

[0093] [Example 3] Synthesis of N-(2-hydroxyethyl)benzylamine Ir-PA (1.29 mg, 2 μmol) was placed in a Schlenk flask and argon purged. Methanol (20 mL), benzaldehyde (2.12 g, 20 mmol), 2-aminoethanol (1.47 g, 24 mmol), and formic acid (2.76 g, 60 mmol) were added. The reaction solution was vigorously stirred at 40°C for 3 hours. The reaction solution was concentrated under reduced pressure to remove the methanol, and then neutralized by adding about 10% aqueous sodium hydroxide solution and extracted three times with ethyl acetate. The ethyl acetate phases were combined, washed with water and then with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was removed by distillation to obtain 2.24 g of the target product. NMR and GC analysis showed that 94% of N-(2-hydroxyethyl)benzylamine was produced in a yield of 70%. 1H NMR (CDCl3,400MHz): δ2.1(br,1H),2.80(m,2H),3.65(m,2H),3.80(s,2H),7.24-7.35(m,5H). 13 C{ 1 H}NMR(CDCl3,100MHz):δ50.5,53.5,60.9,127.1,128.1,128.4,140.1.

[0094] [Example 4] Synthesis of benzylamine N-(2-hydroxyethyl)benzylamine (0.509g, 3.4mmol) was placed in an argon-purged four-neck flask. 10mL of methanol, 10mL of water, 3.4mL of 40% aqueous methylamine solution, and orthoperiodic acid (2g, 8.75mmol) were added and vigorously stirred at room temperature for 18 hours. 5% aqueous sodium hydroxide solution was added to the reaction solution, which was then extracted twice with methylene chloride. The methylene chloride phases were combined, washed with a saturated aqueous sodium thiosulfate solution, dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain the target product. NMR analysis showed that benzylamine was produced. 1 H NMR(CDCl3,400MHz):δ1.5(br,2H),3.87(s,2H),7.22-7.39(m,5H).

[0095] [Example 5] Synthesis of N-(2-hydroxyethyl)-3-bromobenzylamine Ir-PA (0.65 mg, 10 μmol) was placed in a Schlenk flask and replaced with argon. Methanol (50 mL), 3-bromobenzaldehyde (9.25 g, 50 mmol), 2-aminoethanol (3.67 g, 60 mmol), and formic acid (6.91 g, 150 mmol) were added. The reaction solution was vigorously stirred at 40°C for 24 hours. The reaction solution was concentrated under reduced pressure to remove the methanol, and then neutralized by adding approximately 10% aqueous sodium hydroxide solution and extracted three times with ethyl acetate. The ethyl acetate phases were combined, washed with water and then with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was removed by distillation to obtain 11.1 g of the target product. NMR and GC analyses showed that 91% of N-(2-hydroxyethyl)-3-bromobenzylamine was produced in an 88% yield. 1 H NMR (CDCl3,400MHz): δ2.1(br,1H),2.79(m,2H),3.66(m,2H),3.78(s,2H),7.17-7.25(m,2H),7.39(m,1H),7.48(s,1H). 13 C{ 1 H}NMR(CDCl3,100MHz):δ50.5,52.9,61.0,122.5,126.6,130.0,130.1,131.1,142.4.

[0096] [Example 6] Synthesis of 3-bromobenzylamine N-(2-hydroxyethyl)-3-bromobenzylamine (2.77 g, 11.8 mmol) was charged into a four-neck flask purged with argon. 35 mL of methanol, 35 mL of water, 12 mL of 40% aqueous methylamine solution, and sodium periodate (6.55 g, 30.6 mmol) were added and vigorously stirred at room temperature for 20 hours. Insoluble matter was filtered off and washed with methanol, and then the methanol was distilled off under reduced pressure. 5% aqueous sodium hydroxide solution was added, and the mixture was extracted three times with ethyl acetate. The ethyl acetate phases were combined, washed with water and then with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain 2.06 g of the target product. NMR analysis showed that 3-bromobenzylamine was produced in a yield of 94%. 1H NMR (CDCl3,400MHz): δ1.6(br,2H),3.85(s,2H),7.18-7.25(m,2H),7.37(m,1H),7.48(s,1H). 13 C{ 1 H}NMR(CDCl3,100MHz):δ45.9,122.6,125.6,129.8,130.1,130.1,145.5.

[0097] [Example 7] Synthesis of N-(2-hydroxyethyl)-4-cyanobenzylamine Ir-PA (1.29 mg, 2.0 μmol) was placed in a Schlenk flask and argon purged. Methanol (20 mL), 4-cyanobenzaldehyde (2.62 g, 20 mmol), 2-aminoethanol (1.47 g, 24 mmol), and formic acid (2.76 g, 60 mmol) were added. The reaction solution was vigorously stirred at 40°C for 24 hours. The reaction solution was concentrated under reduced pressure to remove the methanol, and then neutralized by adding about 10% aqueous sodium hydroxide solution and extracted three times with ethyl acetate. The ethyl acetate phases were combined, washed with water and then with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was removed by distillation to obtain 2.92 g of the target product. NMR and GC analyses showed that 91% N-(2-hydroxyethyl)-4-cyanobenzylamine was produced in a yield of 75%. 1 H NMR (CDCl3,400MHz): δ2.2(br,1H),2.80(m,2H),3.68(m,2H),3.88(s,2H),7.45(m,2H),7.61(m,2H). 13 C{ 1 H}NMR(CDCl3,100MHz):δ50.6,53.0,61.0,110.7,118.8,128.6,132.2,145.7.

[0098] [Example 8] Synthesis of 4-cyanobenzylamine N-(2-hydroxyethyl)-4-cyanobenzylamine (1.46 g, 8.3 mmol) was charged into a four-neck flask purged with argon. 25 mL of methanol, 25 mL of water, 8.3 mL of 40% aqueous methylamine solution, and sodium periodate (4.62 g, 21.6 mmol) were added and vigorously stirred at room temperature for 20 hours. Insoluble matter was filtered off and washed with methanol, and then the methanol was distilled off under reduced pressure. 5% aqueous sodium hydroxide solution was added, and the mixture was extracted three times with ethyl acetate. The ethyl acetate phases were combined, washed with water and then with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain 0.89 g of the target product. NMR analysis showed that 4-cyanobenzylamine was produced in a yield of 81%. 1 H NMR (CDCl3,400MHz): δ1.5(br,2H),3.96(s,2H),7.45(m,2H),7.63(m,2H). 13 C{ 1 H}NMR(CDCl3,100MHz):δ46.0,110.6,119.0,127.7,132.3,148.4.

[0099] [Example 9] Synthesis of N-(2-hydroxyethyl)-2-phenylpropylamine Ir-PA (1.29 mg, 2.0 μmol) was placed in a Schlenk flask and argon purged. Methanol (20 mL), 2-phenylpropionaldehyde (2.68 g, 20 mmol), 2-aminoethanol (1.47 g, 24 mmol), and formic acid (2.76 g, 60 mmol) were added. The reaction solution was vigorously stirred at 40°C for 22 hours. The reaction solution was concentrated under reduced pressure to remove the methanol, and then neutralized by adding about 5% aqueous sodium hydroxide solution and extracted three times with ethyl acetate. The ethyl acetate phases were combined, washed with water and then with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was removed by distillation to obtain 3.28 g of the target product. NMR and GC analyses showed that 91% N-(2-hydroxyethyl)-2-phenylpropylamine was produced in an 83% yield. 1H NMR (CDCl3,400MHz): δ1.27(d,3H,J=6.8Hz),2.73(m,2H),2.79(dd,2H,J=0.8,7.2Hz),2.91(m,1H),3.55(m,2H),7.20-7.34(m,5H). 13 C{ 1 H}NMR(CDCl3,100MHz):δ19.9,40.1,50.7,56.4,60.6,126.4,127.1,127.2,128.6,145.2.

[0100] [Example 10] Synthesis of 2-phenylpropylamine N-(2-hydroxyethyl)-2-phenylpropylamine (2.38 g, 13.3 mmol) was charged into a four-neck flask purged with argon. 40 mL of methanol, 40 mL of water, 13.5 mL of 40% aqueous methylamine solution, and sodium periodate (7.37 g, 34.5 mmol) were added and vigorously stirred at room temperature for 23 hours. Insoluble matter was filtered off and washed with methanol, and the methanol was distilled off under reduced pressure. 5% aqueous sodium hydroxide solution was added, and the mixture was extracted three times with MTBE. The MTBE phases were combined, washed with water and then with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain 1.61 g of the target product. NMR analysis showed that 2-phenylpropylamine was produced in a yield of 90%. 1 H NMR (CDCl3,400MHz): δ1.1(br,2H),1.25(d,3H,J=7.2Hz),2.74(m,1H),2.85(m,2H),7.20-7.34(m,5H). 13 C{ 1 H}NMR(CDCl3,100MHz):δ19.3,43.6,49.5,126.3,127.3,128.5,145.0.

[0101] [Example 11] Synthesis of N-(2-hydroxyethyl)cyclohexylmethylamine Ir-PA (1.29 mg, 2 μmol) was placed in a Schlenk flask and argon purged. Methanol (20 mL), cyclohexanecarboxaldehyde (2.24 g, 20 mmol), 2-aminoethanol (1.47 g, 24 mmol), and formic acid (2.76 g, 60 mmol) were added. The reaction solution was vigorously stirred at 40°C for 22 hours. The reaction solution was concentrated under reduced pressure to remove the methanol, and then neutralized by adding about 10% aqueous sodium hydroxide solution and extracted three times with ethyl acetate. The ethyl acetate phases were combined, washed with water and then with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was removed by distillation to obtain 2.87 g of the target product. NMR and GC analysis showed that 97% N-(2-hydroxyethyl)cyclohexylmethylamine was produced in an 88% yield. 1 H NMR(CDCl3,400MHz):δ0.86-0.96(m,2H),1.11-1.30(m,3H),1.44(m,1H),1.6 6-1.76(m,5H),2.2(br,1H),2.45(d,2H,J=6.9Hz),2.75(m,2H),3.62(m,2H). 13 C{ 1 H}NMR(CDCl3,100MHz):δ26.0,26.6,31.4,38.0,51.1,56.2,60.7.

[0102] [Example 12] Synthesis of cyclohexylmethylamine N-(2-hydroxyethyl)cyclohexylmethylamine (1.36 g, 8.66 mmol) was placed in a four-neck flask purged with argon. 26 mL of methanol, 26 mL of water, 8.7 mL of 40% aqueous methylamine solution, and sodium periodate (4.81 g, 22.5 mmol) were added and vigorously stirred at room temperature for 21 hours. Insoluble matter was filtered off and washed with methanol, and the methanol was distilled off under reduced pressure. 5% aqueous sodium hydroxide solution was added, and the mixture was extracted three times with diethyl ether. The diethyl ether phases were combined, washed with water and then with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain the target product. NMR analysis showed that cyclohexylmethylamine was produced. 1H NMR (CDCl3,400MHz): δ1.5(br,2H),3.80(s,2H),3.80(s,3H),6.87(m,2H),7.23(m,2H).

[0103] [Example 13] Synthesis of N-(2-hydroxyethyl)-3-benzothienylmethylamine Ir-PA (1.29 mg, 2 μmol) was placed in a Schlenk flask and argon purged. Methanol (2 mL), 3-benzothiophene carboxaldehyde (0.324 g, 2 mmol), 2-aminoethanol (0.147 g, 2.4 mmol), and formic acid (0.276 g, 6 mmol) were added. The reaction solution was vigorously stirred at 40°C for 2 hours. The reaction solution was concentrated under reduced pressure to remove the methanol, and then neutralized by adding about 10% aqueous sodium hydroxide solution and extracted twice with diethyl ether. The diethyl ether phases were combined, washed with water and then with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was removed by distillation to obtain 0.37 g of the target product. NMR and GC analysis showed that 96% N-(2-hydroxyethyl)-3-benzothienylmethylamine was produced in an 83% yield. 1 H NMR (CDCl3,400MHz): δ1.5(br,1H),2.90(m,2H),3.69(m,2H),4.08(s,2H),7.31-7.41(m,3H), 7.82-7.88(m,2H). 13 C{ 1 H}NMR(CDCl3,100MHz):δ47.2,50.7,61.0,121.7,123.0,123.1,124.1,124.4,135.0,138.3,140.7.

[0104] [Example 14] Synthesis of 3-benzothienylmethylamine N-(2-hydroxyethyl)-3-benzothienylmethylamine (0.35g, 1.7mmol) was placed in an argon-purged four-neck flask. 5mL of methanol, 5mL of water, 1.8mL of 40% aqueous methylamine solution, and sodium periodate (0.95g, 4.4mmol) were added and vigorously stirred at room temperature for 17 hours. Insoluble matter was filtered off and washed with methanol, and the methanol was distilled off under reduced pressure. 5% aqueous sodium hydroxide solution was added, and the mixture was extracted three times with methylene chloride. The methylene chloride phases were combined, washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain the target product. NMR analysis showed that 3-benzothienylmethylamine was produced. 1 H NMR (CDCl3,400MHz): δ1.6(br,2H),4.14(s,2H),7.30-7.42(m,3H), 7.77-7.88(m,2H).

[0105] The results are summarized in Table 1. [Table 1]

[0106] [Example 15] Synthesis of N-(2-(1-hydroxy)butyl)-4-methoxybenzylamine Ir-PA (0.53 mg, 0.82 μmol) was placed in a Schlenk flask and argon purged. 41 mL of methanol, 4-methoxybenzaldehyde (5.6 g, 41.1 mmol), 2-amino-1-butanol (4.4 g, 49.4 mmol), and formic acid (5.68 g, 123 mmol) were added. The reaction solution was vigorously stirred at 40°C for 24 hours. The reaction solution was concentrated under reduced pressure to remove the methanol, and then neutralized by adding about 10% aqueous sodium hydroxide solution and extracted three times with ethyl acetate. The ethyl acetate phases were combined, washed with water and then with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was removed by distillation to obtain 8.77 g of the target product. NMR and GC analysis showed that 96% of N-(2-(1-hydroxy)butyl)-4-methoxybenzylamine was produced in an 88% yield. 1H NMR(CDCl3,400MHz):δ0.92(t,3H,J=7.3Hz),1.39-1.60(m,2H),2.62(m,1H),3.31(dd,1H,J=6.4, 10.5Hz),3.65(dd,1H,J=3.7,10.5Hz),3.68-3.78(m,2H),3.80(s,3H),6.87(m,2H),7.24(m,2H). The structural formula is as follows: [ka]

[0107] [Example 16] Synthesis of 4-methoxybenzylamine N-(2-(1-hydroxy)butyl)-4-methoxybenzylamine (5.08 g, 24.3 mmol) was charged into a four-neck flask purged with argon. 73 mL of methanol, 73 mL of water, 24 mL of 40% aqueous methylamine solution, and sodium periodate (13.5 g, 63.1 mmol) were added and vigorously stirred at room temperature for 18 hours. Insoluble matter was filtered off and washed with methanol, and then the methanol was distilled off under reduced pressure. 5% aqueous sodium hydroxide solution was added, and the mixture was extracted three times with ethyl acetate. The ethyl acetate phases were combined, washed with water and then with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain 3.39 g of the target product. NMR analysis showed that 4-methoxybenzylamine was produced in a yield of 81%.

[0108] [Example 17] Synthesis of N,N-di(2-hydroxyethyl)-3-phenylpropylamine Ir-QN2 (1.1 mg, 2 μmol) was placed in a Schlenk flask and argon purged. 20 mL of methanol, 3-phenylpropionaldehyde (2.68 g, 20 mmol), diethanolamine (2.52 g, 24 mmol), and formic acid (2.76 g, 60 mmol) were added. The reaction solution was vigorously stirred at 40°C for 21 hours. The reaction solution was concentrated under reduced pressure to remove the methanol, and then neutralized by adding approximately 10% aqueous sodium hydroxide solution and extracted three times with ethyl acetate. The ethyl acetate phases were combined, washed with water and then with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was removed by distillation to obtain 3.99 g of the target product. NMR and GC analyses showed that 93% of N,N-di(2-hydroxyethyl)-3-phenylpropylamine was produced in an 83% yield. 1 H NMR (CDCl3,400MHz): δ1.81(m,2H),2.56-2.64(m,4H),2.65(m,4H),3.60(m,4H),7.17-7.30(m,5H). 13 C{ 1 H}NMR(CDCl3,100MHz):δ28.7,33.5,54.2,56.0,59.7,125.9,128.3,128.4,141.8. The structural formula is as follows: [ka]

[0109] [Example 18] Synthesis of N-(2-hydroxyethyl)-N-methyl-3-phenylpropylamine Ir-QN2 (1.1 mg, 2 μmol) was placed in a Schlenk flask and argon purged. 20 mL of methanol, 3-phenylpropionaldehyde (2.68 g, 20 mmol), N-methyl-2-aminoethanol (1.8 g, 24 mmol), and formic acid (2.76 g, 60 mmol) were added. The reaction solution was vigorously stirred at 40°C for 21 hours. The reaction solution was concentrated under reduced pressure to remove the methanol, and then neutralized by adding approximately 10% aqueous sodium hydroxide solution and extracted three times with ethyl acetate. The ethyl acetate phases were combined, washed with water and then with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was removed by distillation to obtain 3.54 g of the target product. NMR and GC analysis showed that 90% of N-(2-hydroxyethyl)-N-methyl-3-phenylpropylamine was produced in an 82% yield. 1 H NMR (CDCl3,400MHz): δ1.81(m,2H),2.24(s,3H),2.44(m,2H),2.52(m,2H),2.63(m,2H),2.9(br,1H),3.57(m,2H),7.18-7.30(m,5H). 13 C{ 1 H}NMR(CDCl3,100MHz):δ29.0,33.5,41.4,57.1,58.3,58.7,125.8,128.3,128.3,142.1. The structural formula is as follows: [ka]

[0110] [Example 19] Synthesis of N-(2-hydroxyethyl)-4-methoxybenzylamine Ir-QN1 (1.01 mg, 2 μmol) was placed in a Schlenk flask and argon purged. Methanol (2 mL), para-anisaldehyde (0.27 g, 2 mmol), 2-aminoethanol (0.15 g, 2.4 mmol), and formic acid (0.28 g, 6 mmol) were added. The reaction solution was vigorously stirred at 40°C for 24 hours. The reaction solution was concentrated under reduced pressure to remove the methanol, and then neutralized by adding approximately 10% aqueous sodium hydroxide solution and extracted three times with ethyl acetate. The ethyl acetate phases were combined, washed with water and then with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was removed by distillation to obtain 0.27 g of the target product. NMR analysis showed that N-(2-hydroxyethyl)-4-methoxybenzylamine was produced in a yield of 73%.

[0111] [Example 20] Synthesis of N-(2-hydroxyethyl)-4-methoxybenzylamine Ir-PSA (1.33 mg, 2 μmol) was placed in a Schlenk flask and replaced with argon. Methanol (2 mL), para-anisaldehyde (0.27 g, 2 mmol), 2-aminoethanol (0.15 g, 2.4 mmol), and formic acid (0.28 g, 6 mmol) were added. The reaction solution was vigorously stirred at 40°C for 24 hours. The reaction solution was concentrated under reduced pressure to remove the methanol, and N-(2-hydroxyethyl)-4-methoxybenzylamine was produced.

[0112] [Example 21] Synthesis of N-(2-hydroxyethyl)-4-methoxybenzylamine Ir-CA (1.23 mg, 2 μmol) was placed in a Schlenk flask and replaced with argon. Methanol (2 mL), para-anisaldehyde (0.27 g, 2 mmol), 2-aminoethanol (0.15 g, 2.4 mmol), and formic acid (0.28 g, 6 mmol) were added. The reaction solution was vigorously stirred at 40°C for 24 hours. The reaction solution was concentrated under reduced pressure to remove the methanol, and N-(2-hydroxyethyl)-4-methoxybenzylamine was produced.

[0113] [Example 22] Synthesis of 2-(4-methoxyphenyl)oxazolidine Molecular sieves 3A (4.6 g) was placed in an argon-purged Schlenk flask. 25 mL of toluene, 4-methoxybenzaldehyde (3.40 g, 25 mmol), and 2-aminoethanol (1.83 g, 30 mmol) were added and stirred at room temperature for 18 hours. Insoluble matter was filtered off and washed with toluene, and the toluene was then distilled off under reduced pressure to obtain 4.48 g of the target product. NMR analysis showed that 2-(4-methoxyphenyl)oxazolidine was produced in a yield of 99%. 1 H NMR (CDCl3,400MHz): δ2.1(br,1H),3.73(m,2H),3.85(s,3H),3.90(m,2h),6.93(m,2H),7.68(m,2H),8.28(s,1H).

[0114] [Example 23] Synthesis of N-(2-hydroxyethyl)-4-methoxybenzylamine In an argon-substituted Schlenk flask, 2-(4-methoxyphenyl)oxazolidine (2.66 g, 15 mmol) was added with Ir-PA (0.19 mg, 0.3 μmol), methanol (15 mL), and formic acid (2.1 g, 45 mmol). The reaction solution was vigorously stirred at 40° C. for 24 hours. The reaction solution was concentrated under reduced pressure to remove the methanol, and then neutralized with approximately 10% aqueous sodium hydroxide solution, and extracted three times with ethyl acetate. The ethyl acetate phases were combined, washed with water and then with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was removed by distillation to obtain the target product. NMR analysis showed that 89% of N-(2-hydroxyethyl)-4-methoxybenzylamine was produced.

Claims

1. A method for producing a primary or secondary amine compound, comprising the steps of: The following general formula (1) 【Chemistry 1】 In the formula, R １ represents a hydrogen atom, a C1-C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 22 ring members whose carbon atoms may be replaced by heteroatoms, or a heterocyclyl group having 3 to 20 ring members, in which one or more hydrogen atoms are optionally substituted by a substituent W, W is a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 alkylsulfenyl group, a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, a sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, two or more Ws may be joined together to form one or more rings, Ra, Rb and Rc are the same or different and each represent a hydrogen atom, a C1-C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, an aralkyl group having 6 to 20 ring members, a heteroaralkyl group having 6 to 20 ring members, an alkylaryl group having 6 to 20 ring members, or an alkylheteroaryl group having 6 to 20 ring members; R ２ , R ３ , R ４ and R ５ are the same or different and each is a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, or an aryl group having 6 to 22 ring members, wherein a carbon atom may be replaced by a heteroatom, n is 1 or 2; When n is 2, R １ does not exist, and an amino alcohol represented by the formula: The following general formula (2) 【Chemistry 2】 In the formula, R ６ represents a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by heteroatoms, a heterocyclyl group having 3 to 20 ring members, -COOH, a carbamoyl group, an acetyl group, or a benzoyl group, in which one or more hydrogen atoms are optionally substituted by a substituent W; Ra, Rb and Rc have the same meanings as above. and an aldehyde represented by The following general formula (3) 【Chemistry 3】 In the formula, Ar is a cyclopentadienyl group in which one or more hydrogen atoms may be substituted by the substituent W. X is a hydride group or an anionic group; R ７ and R ８ are the same or different and each represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 alkylsulfenyl group, a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, a sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, and one or more hydrogen atoms of these groups may be replaced by the substituent W, Ra, Rb and Rc have the same meanings as above, j and k are the same or different and are integers from 0 to 3; R ７ Or R ８ a carbon atom in the quinoline ring to which is not attached may be replaced by a nitrogen atom, When j is 2 or more, 2 or more R ７ may be joined together to form one or more rings, The following general formula (4) 【Chemistry 4】 In the formula, Ar, X and R ７ has the same meaning as above, R ９ represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by heteroatoms, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 alkylsulfenyl group, a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, a sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, one or more hydrogen atoms of these groups may be replaced by the substituent W, Ra, Rb and Rc have the same meanings as above, l is an integer from 0 to 4; R ７ a carbon atom in the pyridine ring to which is not bonded may be replaced by a nitrogen atom, When l is 2 or more, 2 or more R ７ may be joined together to form one or more rings, The following general formula (5) 【Chemistry 5】 In the formula, Ar, X, R ７ , l has the same meaning as above, R １０ and R １１ are the same or different and each represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 alkylsulfenyl group, a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, a sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, and one or more hydrogen atoms of these groups may be replaced by the substituent W, R １０ and R １１ and may be taken together to form a ring, R １２ represents a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, -C(=O)-Ra or -C(=O)-NRaRb, in which one or more hydrogen atoms may be substituted by the substituent W; Ra, Rb and Rc have the same meanings as above, R ７ a carbon atom in the pyridine ring to which is not bonded may be replaced by a nitrogen atom, When l is 2 or more, 2 or more R ７ may be joined together to form one or more rings, or The following general formula (6) 【Chemistry 6】 In the formula, Ar and X have the same meanings as defined above. A is a saturated or unsaturated nitrogen-containing heterocyclic carbene containing at least two nitrogen atoms, in which one or more hydrogen atoms may be substituted with the substituent W; R １３ , R １４ , R １５ , R １６ and R １７ are the same or different and each represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 alkylsulfenyl group, a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, a sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, and one or more hydrogen atoms of these groups may be replaced by the substituent W, R １８ represents a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, -C(=O)-Ra, -C(=O)-ORa, -C(=O)-NRaRb, -C(=S)-NRaRb, a C1 to C20 fluoroalkyl group, or an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, and one or more hydrogen atoms of these groups are optionally substituted by the substituent W, Ra, Rb and Rc have the same meanings as above. With a hydrogen donor compound in the presence of an organic iridium compound represented by the formula: The reaction product is represented by the following general formula (A): 【Chemistry 7】 In the formula, R ２ , R ３ , R ４ , R ５ and n has the same meaning as in general formula (1); a step of oxidatively deprotecting the moiety represented by The method according to claim 1, further comprising:

2. A method for producing a primary or secondary amine compound, comprising the steps of: The following general formula (1) 【Chemistry 8】 In the formula, R １ represents a hydrogen atom, a C1-C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 22 ring members whose carbon atoms may be replaced by heteroatoms, or a heterocyclyl group having 3 to 20 ring members, one or more hydrogen atoms of these groups may be replaced by the substituent W, W is a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 alkylsulfenyl group, a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, a sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, two or more Ws may be joined together to form one or more rings, Ra, Rb and Rc are the same or different and each represent a hydrogen atom, a C1-C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, an aralkyl group having 6 to 20 ring members, a heteroaralkyl group having 6 to 20 ring members, an alkylaryl group having 6 to 20 ring members, or an alkylheteroaryl group having 6 to 20 ring members; R ２ , R ３ , R ４ and R ５ are the same or different and each is a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, or an aryl group having 6 to 22 ring members, wherein a carbon atom may be replaced by a heteroatom, n is 1 or 2; When n is 2, R １ does not exist, and an amino alcohol represented by the formula: The following general formula (2) 【Chemistry 9】 In the formula, R ６ represents a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by heteroatoms, a heterocyclyl group having 3 to 20 ring members, -COOH, a carbamoyl group, an acetyl group, or a benzoyl group, in which one or more hydrogen atoms are optionally substituted by the substituent W; Ra, Rb and Rc have the same meanings as above. and an aldehyde represented by The following general formula (7) 【Chemistry 10】 In the formula, Ar is a cyclopentadienyl group in which one or more hydrogen atoms may be substituted by the substituent W. X is a hydride group or an anionic group; and an organic iridium compound represented by the formula: The following general formula (8) 【Chemistry 11】 In the formula, R ７ and R ８ are the same or different and each represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 alkylsulfenyl group, a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, a sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, and one or more hydrogen atoms of these groups may be replaced by the substituent W, Ra, Rb and Rc have the same meanings as above, j and k are the same or different and are integers from 0 to 3; R ７ Or R ８ a carbon atom in the quinoline ring to which is not attached may be replaced by a nitrogen atom, When j is 2 or more, 2 or more R ７ may be joined together to form one or more rings, The following general formula (9) 【Chemistry 12】 In the formula, R ７ has the same meaning as above, R ９ represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by heteroatoms, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 alkylsulfenyl group, a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, a sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, and one or more hydrogen atoms of these groups may be replaced by the substituent W, Ra, Rb and Rc have the same meanings as above, l is an integer from 0 to 4; R ７ a carbon atom in the pyridine ring to which is not bonded may be replaced by a nitrogen atom, When l is 2 or more, 2 or more R ７ may be joined together to form one or more rings, The following general formula (10) 【Chemistry 13】 In the formula, R ７ and l has the same meaning as above, R １０ and R １１ are the same or different and each represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 alkylsulfenyl group, a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, a sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, and one or more hydrogen atoms of these groups may be replaced by the substituent W, R １０ and R １１ and may be taken together to form a ring, R １２ represents a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, -C(=O)-Ra or -C(=O)-NRaRb, in which one or more hydrogen atoms may be substituted by the substituent W; Ra, Rb and Rc have the same meanings as above, R ７ a carbon atom in the pyridine ring to which is not bonded may be replaced by a nitrogen atom, When l is 2 or more, 2 or more R ７ may be joined together to form one or more rings, or The following general formula (11) 【Chemistry 14】 In the formula, R １３ , R １４ , R １５ , R １６ and R １７ are the same or different and each represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 alkylsulfenyl group, a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, a sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, and one or more hydrogen atoms of these groups may be replaced by the substituent W, R １８ represents a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, -C(=O)-Ra, -C(=O)-ORa, -C(=O)-NRaRb, -C(=S)-NRaRb, a C1 to C20 fluoroalkyl group, or an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, and one or more hydrogen atoms of these groups may be replaced by the substituent W; A' is a saturated or unsaturated nitrogen-containing heterocyclic carbene precursor containing at least two nitrogen atoms, in which one or more hydrogen atoms may be substituted with the substituent W; Ra, Rb and Rc have the same meanings as above. Y is an anionic group; with a hydrogen donor compound in the presence of an organic compound represented by the formula: The reaction product is represented by the following general formula (A): 【Chemistry 15】 In the formula, R ２ , R ３ , R ４ , R ５ and n has the same meaning as in general formula (1); a step of oxidatively deprotecting the moiety represented by The method according to claim 1, further comprising:

3. 1. A method for producing primary and secondary amine compounds, comprising the steps of: The following general formula (1) 【Chemistry 16】 In the formula, R １ represents a hydrogen atom, a C1-C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 22 ring members whose carbon atoms may be replaced by heteroatoms, or a heterocyclyl group having 3 to 20 ring members, one or more hydrogen atoms of these groups may be replaced by the substituent W, W is a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 alkylsulfenyl group, a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, a sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, two or more Ws may be joined together to form one or more rings, Ra, Rb and Rc are the same or different and each represent a hydrogen atom, a C1-C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, an aralkyl group having 6 to 20 ring members, a heteroaralkyl group having 6 to 20 ring members, an alkylaryl group having 6 to 20 ring members, or an alkylheteroaryl group having 6 to 20 ring members; R ２ , R ３ , R ４ and R ５ are the same or different and each is a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, or an aryl group having 6 to 22 ring members, wherein a carbon atom may be replaced by a heteroatom, n is 1 or 2; When n is 2, R １ does not exist, and an amino alcohol represented by the formula: The following general formula (2) 【Chemistry 17】 In the formula, R ６ represents a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by heteroatoms, a heterocyclyl group having 3 to 20 ring members, -COOH, a carbamoyl group, an acetyl group, or a benzoyl group, in which one or more hydrogen atoms are optionally substituted by the substituent W; Ra, Rb and Rc have the same meanings as above. A hemiaminal ether, imine, or enamine prepared from an aldehyde represented by the formula: The following general formula (3) 【Chemistry 18】 In the formula, Ar is a cyclopentadienyl group in which one or more hydrogen atoms may be substituted by the substituent W. X is a hydride group or an anionic group; R ７ and R ８ are the same or different and each represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 alkylsulfenyl group, a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, a sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, and one or more hydrogen atoms of these groups may be replaced by the substituent W, Ra, Rb and Rc have the same meanings as above, j and k are the same or different and are integers from 0 to 3; R ７ Or R ８ a carbon atom in the quinoline ring to which is not attached may be replaced by a nitrogen atom, When j is 2 or more, 2 or more R ７ may be joined together to form one or more rings, The following general formula (4) 【Chemistry 19】 In the formula, Ar, X and R ７ has the same meaning as above, R ９ represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by heteroatoms, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 alkylsulfenyl group, a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, a sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, one or more hydrogen atoms of these groups may be replaced by the substituent W, Ra, Rb and Rc have the same meanings as above, l is an integer from 0 to 4; R ７ a carbon atom in the pyridine ring to which is not bonded may be replaced by a nitrogen atom, When l is 2 or more, 2 or more R ７ may be joined together to form one or more rings, The following general formula (5) 【Chemistry 20】 In the formula, Ar, X, R ７ , l has the same meaning as above, R １０ and R １１ are the same or different and each represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 alkylsulfenyl group, a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, a sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, and one or more hydrogen atoms of these groups may be replaced by the substituent W, R １０ and R １１ and may be taken together to form a ring, R １２ represents a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, -C(=O)-Ra or -C(=O)-NRaRb, in which one or more hydrogen atoms may be substituted by the substituent W; Ra, Rb and Rc have the same meanings as above, R ７ a carbon atom in the pyridine ring to which is not bonded may be replaced by a nitrogen atom, When l is 2 or more, 2 or more R ７ may be joined together to form one or more rings, or The following general formula (6) 【Chemistry 21】 In the formula, Ar and X have the same meanings as defined above. A is a saturated or unsaturated nitrogen-containing heterocyclic carbene containing at least two nitrogen atoms, in which one or more hydrogen atoms may be substituted with the substituent W; R １３ , R １４ , R １５ , R １６ and R １７ are the same or different and each represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 alkylsulfenyl group, a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, a sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, and one or more hydrogen atoms of these groups may be replaced by the substituent W, R １８ represents a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, -C(=O)-Ra, -C(=O)-ORa, -C(=O)-NRaRb, -C(=S)-NRaRb, a C1 to C20 fluoroalkyl group, or an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, and one or more hydrogen atoms of these groups are optionally substituted by the substituent W, Ra, Rb and Rc have the same meanings as above. With a hydrogen donor compound in the presence of an organic iridium compound represented by the formula: The reaction product is represented by the following general formula (A): 【Chemical 22】 In the formula, R ２ , R ３ , R ４ , R ５ and n has the same meaning as in general formula (1); a step of oxidatively deprotecting the moiety represented by The method according to claim 1, further comprising:

4. 1. A method for producing primary and secondary amine compounds, comprising the steps of: The following general formula (1) 【Chemistry 23】 In the formula, R １ represents a hydrogen atom, a C1-C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 22 ring members whose carbon atoms may be replaced by heteroatoms, or a heterocyclyl group having 3 to 20 ring members, one or more hydrogen atoms of these groups may be replaced by the substituent W, W is a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 alkylsulfenyl group, a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, a sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, two or more Ws may be joined together to form one or more rings, Ra, Rb and Rc are the same or different and each represent a hydrogen atom, a C1-C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, an aralkyl group having 6 to 20 ring members, a heteroaralkyl group having 6 to 20 ring members, an alkylaryl group having 6 to 20 ring members, or an alkylheteroaryl group having 6 to 20 ring members; R ２ , R ３ , R ４ and R ５ are the same or different and each is a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, or an aryl group having 6 to 22 ring members, wherein a carbon atom may be replaced by a heteroatom, n is 1 or 2; When n is 2, R １ is not present, and The following general formula (2) 【Chemistry 24】 In the formula, R ６ represents a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by heteroatoms, a heterocyclyl group having 3 to 20 ring members, -COOH, a carbamoyl group, an acetyl group, or a benzoyl group, in which one or more hydrogen atoms are optionally substituted by the substituent W; Ra, Rb and Rc have the same meanings as above. A hemiaminal ether, imine, or enamine prepared from an aldehyde represented by the formula: The following general formula (7) 【Chemistry 25】 In the formula, Ar is a cyclopentadienyl group in which one or more hydrogen atoms may be substituted by the substituent W. X is a hydride group or an anionic group; and an organic iridium compound represented by the formula: The following general formula (8) 【Chemistry 26】 In the formula, R ７ and R ８ are the same or different and each represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 alkylsulfenyl group, a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, a sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, and one or more hydrogen atoms of these groups may be replaced by the substituent W, Ra, Rb and Rc have the same meanings as above, j and k are the same or different and are integers from 0 to 3; R ７ Or R ８ a carbon atom in the quinoline ring to which is not attached may be replaced by a nitrogen atom, When j is 2 or more, 2 or more R ７ may be joined together to form one or more rings, The following general formula (9) 【Chemical 27】 In the formula, R ７ has the same meaning as above, R ９ represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by heteroatoms, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 alkylsulfenyl group, a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, a sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, and one or more hydrogen atoms of these groups may be replaced by the substituent W, Ra, Rb and Rc have the same meanings as above, l is an integer from 0 to 4; R ７ a carbon atom in the pyridine ring to which is not bonded may be replaced by a nitrogen atom, When l is 2 or more, 2 or more R ７ may be joined together to form one or more rings, The following general formula (10) 【Chemistry 28】 During the ceremony, R ７ and l has the same meaning as above, R １０ and R １１ are the same or different and each represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 alkylsulfenyl group, a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, a sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, and one or more hydrogen atoms of these groups may be replaced by the substituent W, R １０ and R １１ and may be taken together to form a ring, R １２ represents a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, -C(=O)-Ra or -C(=O)-NRaRb, in which one or more hydrogen atoms may be substituted by the substituent W; Ra, Rb and Rc have the same meanings as above, R ７ a carbon atom in the pyridine ring to which is not bonded may be replaced by a nitrogen atom, When l is 2 or more, 2 or more R ７ may be joined together to form one or more rings, or The following general formula (11) 【Chemical 29】 In the formula, R １３ , R １４ , R １５ , R １６ and R １７ are the same or different and each represents a hydrogen atom, a C1 to C20 saturated or unsaturated hydrocarbon group, an aryl group having 6 to 20 ring members whose carbon atoms may be replaced by a heteroatom, a heterocyclyl group having 3 to 20 ring members, a C1 to C20 alkoxy group, -C(=O)-Ra, -C(=O)-ORa, -OC(=O)-Ra, a hydroxyl group, -NRaRb, -C(=O)-NRaRb, -NRa-C(=O)-Rb, a nitro group, a cyano group, -PRaRb, a C1 to C20 alkylsulfenyl group, a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, a sulfo group, a mercapto group, -SiRaRbRc, a halogen group, or a C1 to C20 fluoroalkyl group, and one or more hydrogen atoms of these groups may be replaced by the substituent W, R １８ represents a C1 to C20 alkylsulfonyl group, a benzenesulfonyl group, -C(=O)-Ra, -C(=O)-ORa, -C(=O)-NRaRb, -C(=S)-NRaRb, a C1 to C20 fluoroalkyl group, or an aryl group having 6 to 20 ring members in which a carbon atom may be replaced by a heteroatom, and one or more hydrogen atoms of these groups may be replaced by the substituent W; A' is a saturated or unsaturated nitrogen-containing heterocyclic carbene precursor containing at least two nitrogen atoms, in which one or more hydrogen atoms may be substituted with the substituent W; Ra, Rb and Rc have the same meanings as above. Y is an anionic group; with a hydrogen donor compound in the presence of an organic compound represented by the formula: The reaction product is represented by the following general formula (A): 【Chemistry 30】 In the formula, R ２ , R ３ , R ４ , R ５ and n has the same meaning as in general formula (1); a step of oxidatively deprotecting the moiety represented by The method according to claim 1, further comprising:

5. The method according to any one of claims 1 to 4, wherein the aminoalcohol represented by the general formula (1) is 2-aminoethanol, 2-amino-1-propanol, 2-amino-1-butanol, valinol or phenylglycinol.

6. The process according to any one of claims 1 to 5, wherein the oxidative deprotection is carried out using periodic acid, periodate or lead tetraacetate as oxidizing agent.

7. The method according to any one of claims 1 to 6, wherein the hydrogen donating compound is formic acid or a formate.

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