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Process for production of 4-aminotetrahydropyrans and salts thereof with acids, intermediates for the process, and process for production thereof

A technology of aminotetrahydropyran compound and tetrahydropyran compound, applied in organic chemistry methods, organic chemistry, etc., can solve the problems of complex reaction operation, complex reaction system, and low yield of target products

Inactive Publication Date: 2006-08-23
UBE IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are following problems in this method: a far excess ammonia source (for example, ammonium acetate) must be used, and because the reaction system is complex, the reaction operation is complicated, and the yield of the target substance is low
[0003] In addition, 2-substituted tetrahydropyran-4-sulfonates, which can be used as synthetic raw materials for the above-mentioned compounds, and their production methods are not known at all.

Method used

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  • Process for production of 4-aminotetrahydropyrans and salts thereof with acids, intermediates for the process, and process for production thereof
  • Process for production of 4-aminotetrahydropyrans and salts thereof with acids, intermediates for the process, and process for production thereof
  • Process for production of 4-aminotetrahydropyrans and salts thereof with acids, intermediates for the process, and process for production thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] (1) Synthesis of 4-hydrazinotetrahydropyran

[0073] In a glass flask with a stirring device, a thermometer and a reflux condenser with an inner volume of 500ml, add 134.7g (710mmol) of tetrahydropyran-4-methanesulfonate with a purity of 95%, 256ml (5.27mol) of Hydrazine monohydrate (hydrazine monohydrate) and 256 ml of ethanol were reacted at 70-80° C. for 3 hours under a nitrogen atmosphere while stirring. After the reaction, the reaction liquid was cooled to room temperature, and after adding 98 ml (784 mmol) of 8 mol / l sodium hydroxide aqueous solution, it was concentrated under reduced pressure. After adding 500 ml of toluene to the concentrate, it was filtered, and the filtrate was again concentrated under reduced pressure. The precipitated solid was filtered off to obtain 45.0 g of 4-hydrazinotetrahydropyran with a purity of 93% (area percentage according to gas chromatography) (isolation yield: 51%) as a yellow liquid.

[0074] The physical property values ​​o...

Embodiment 2

[0080] (1) Synthesis of 4-hydrazinotetrahydropyran hydrochloride

[0081] In a glass flask with a stirring device, a thermometer and a reflux condenser with an inner volume of 200ml, add 10.0g (50mmol) of tetrahydropyran-4-methanesulfonate with a purity of 95%, 26ml (530mmol) of hydrazine monohydrate The material and 26ml of ethanol were reacted at 75° C. for 3 hours under a nitrogen atmosphere while stirring. After completion of the reaction, the reaction liquid was cooled to room temperature, and after adding 14 g (72.6 mmol) of 28% by weight sodium methoxide methanol solution, it was concentrated under reduced pressure. After adding 50 ml of toluene to the concentrate, it was filtered, and the filtrate was again concentrated under reduced pressure. The concentrate was cooled to 0° C., added with 50 ml of methanol and 6.5 ml (78 mmol) of 12 mol / l hydrochloric acid, and then concentrated under reduced pressure. The concentrate was recrystallized using ethanol and toluene to...

Embodiment 3

[0091] Synthesis of 4-aminotetrahydropyran hydrochloride

[0092] In a glass flask with a stirring device, a thermometer and a reflux condenser with an inner volume of 50ml, add 1.0g (6.55mmol) of 4-hydrazinotetrahydro with a purity of 99% synthesized in the same manner as in Example 2 (2) above Pyran, 200 mg of developed Raney nickel and 5 ml of ethanol were reacted in an argon atmosphere at 75° C. for 20 hours. After the reaction, the reaction solution was cooled to room temperature, the reaction solution was filtered, and the filtrate was analyzed by gas chromatography (internal standard method) to find that 246 mg of 4-aminotetrahydropyran was generated (reaction yield: 37%).

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Abstract

A process for the production of 4-aminotetrahydropyrans represented by the general formula (2) and salts thereof with acids: [wherein R is hydrogen or a hydrocarbon group], characterized by subjecting a 4-hydrazinotetrahydropyran represented by the general formula (1) or a salt thereof with an acid: [wherein R is as defined above] to decomposition in the presence of at least one compound selected from among Raney nickel, noble metal catalysts, and metal oxides; intermediates for the process; and a process for the production of the intermediates.

Description

technical field [0001] The present invention relates to a new production method of 4-aminotetrahydropyran compound and its acid salt. 4-Aminotetrahydropyran compounds and salts thereof are compounds useful as raw materials for the synthesis of pharmaceuticals, agricultural chemicals, and the like. The present invention also relates to 2-substituted tetrahydropyran-4-sulfonates and methods for their production. 2-Substituted tetrahydropyran-4-sulfonates are useful compounds as raw materials for pharmaceuticals, agricultural chemicals, etc., or as synthetic intermediates. Background technique [0002] At present, as a method for producing 4-aminotetrahydropyran compounds and salts thereof, it has been disclosed that tetrahydropyran-4-one, ammonium acetate, molecular sieve powder, and sodium cyanoborohydride are reacted in ethanol to produce 12 % yield to obtain 4-aminotetrahydropyran (for example, refer to Japanese Patent Application Laid-Open No. H11-510180 (pp. 66-67)). H...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/14C07B61/00C07D309/10
CPCC07D309/10C07D309/14
Inventor 西野繁荣弘津健二岛秀好岩本圭司原田崇司铃木忍
Owner UBE IND LTD
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