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Chirality N, N-dialkyl-1, 2-diaminocyclohexane catalyst as well as preparation method and application thereof

A cyclohexanediamine catalyst and cyclohexanediamine technology are used in the preparation of amino compounds, the preparation of carbon-based compounds, chemical instruments and methods, etc., to achieve the effect of mild reaction conditions

Active Publication Date: 2013-05-22
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the above-mentioned chiral cyclohexanediamine catalyst has achieved good results, it has also encountered some problems, such as the amount of catalyst, reaction time and optical activity of the product, which still have a certain distance from the actual production requirements.

Method used

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  • Chirality N, N-dialkyl-1, 2-diaminocyclohexane catalyst as well as preparation method and application thereof
  • Chirality N, N-dialkyl-1, 2-diaminocyclohexane catalyst as well as preparation method and application thereof
  • Chirality N, N-dialkyl-1, 2-diaminocyclohexane catalyst as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1. (1R,2R)-N 1 -Butyl-N 1 - Preparation of methyl-1,2-cyclohexanediamine dihydrochloride (1a·2HCl).

[0036] (1R,2R)-N 1 -Butyl-N 1 -The structural formula of methyl-1,2-cyclohexanediamine dihydrochloride (1a 2HCl) is as follows:

[0037]

[0038] Concrete preparation steps are as follows:

[0039] Add 10mmol of (1R,2R)-1,2-cyclohexanediamine protected by mono-tert-butoxycarbonyl and 50mmol of n-butyraldehyde into 50mL of methanol, and react at 0~20°C for 4~5 hours. The reaction solution was cooled in an ice bath, and then 30 mmol NaBH 4 Add in batches, continue to react for 0.5 hours, and then heat to 25°C for 3 hours to obtain intermediate 3a (the product does not need to be isolated). Add 20mmolNaBH to the reaction solution 3 (CN), 2.4mL formaldehyde solution with mass percent concentration of 37%, reacted at 30°C for 5 hours. The solvent was removed under reduced pressure, 40 mL of 1 mol / L NaOH aqueous solution was added, and 50 mL of ethyl acetate ...

Embodiment 2

[0042] Example 2. (1R,2R)-N 1 -Isobutyl-N 1 - Preparation of methyl-1,2-cyclohexanediamine dihydrochloride (1b·2HCl).

[0043] (1R,2R)-N 1 -Isobutyl-N 1 -The structural formula of methyl-1,2-cyclohexanediamine dihydrochloride (1b 2HCl) is as follows:

[0044]

[0045] Concrete preparation steps are as follows:

[0046] Add 10mmol of (1R,2R)-1,2-cyclohexanediamine protected by mono-tert-butoxycarbonyl and 50mmol of isobutyraldehyde into 50mL of methanol solution, and react at 20~40°C for 3~4 hours. The reaction solution was cooled in an ice bath, and then 30 mmol NaBH 4 Add in batches, continue to react for 1.5 hours, and then heat to 40°C for 2 hours to obtain intermediate 3b (the product does not need to be isolated). Add 20mmolNaBH to the reaction solution 3 (CN), 2.4mL formaldehyde solution with mass percent concentration of 37%, reacted at 25°C for 8 hours. The solvent was removed under reduced pressure, 40 mL of 1 mol / L NaOH aqueous solution was added, and 50 m...

Embodiment 3

[0049] Example 3. (1R,2R)-N 1 -(2-Pentyl)-N 1 - Preparation of methyl-1,2-cyclohexanediamine dihydrochloride (1c·2HCl).

[0050] (1R,2R)-N 1 -(2-Pentyl)-N 1 -The structural formula of methyl-1,2-cyclohexanediamine dihydrochloride (1c 2HCl) is as follows:

[0051]

[0052] Concrete preparation steps are as follows:

[0053] Add 10mmol of (1R,2R)-1,2-cyclohexanediamine protected by mono-tert-butoxycarbonyl and 50mmol of 2-pentanone into 50mL of methanol solution, and react at 40~60°C for 2~3 hours. The reaction solution was cooled in an ice bath, and then 30 mmol NaBH 4 Added in batches, continued to react for 2 hours, and then heated to 60°C for 0.5 hours to obtain intermediate 3c (the product does not need to be isolated). Add 20mmolNaBH to the reaction solution 3 (CN), 2.4mL formaldehyde solution with mass percent concentration of 37%, reacted at 20°C for 12 hours. The solvent was removed under reduced pressure, 40 mL of 1 mol / L NaOH aqueous solution was added, and...

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Abstract

The invention discloses a chirality N, N-dialkyl-1, 2-diaminocyclohexane catalyst (I), a preparation method of the catalyst and also an application of the catalyst in asymmetric aldol reaction, belonging to the technical field of catalysts.

Description

technical field [0001] The invention belongs to the technical field of catalysts, and in particular relates to a novel chiral N,N-dialkyl-1,2-cyclohexanediamine catalyst, its preparation method and its catalytic application in asymmetric aldol condensation reaction. Background technique [0002] Aldol condensation reaction (aldol reaction), that is, an aldehyde or ketone with α-H, generates a carbanion under the catalysis of a base, and then the carbanion acts as a nucleophile to perform nucleophilic addition to the aldehyde or ketone to generate a β-hydroxy ketone condensation reaction. This reaction can also be carried out under the catalysis of weak acids, which is the simplest chemical transformation to construct asymmetric C-C bonds, and at the same time can meet the most stringent requirements of asymmetric methodology. The basic unit with β-hydroxyl in its reaction product occupies a very important position in the synthesis of natural products and biologically active...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/02C07C211/36C07C209/62C07C205/45C07C201/12C07C49/747C07C49/753C07C45/68C07C255/56C07C253/30
Inventor 苟少华李磊
Owner SOUTHEAST UNIV
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