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Eco-friendly process for the preparation of chiral alcohols by asymmetric reduction of prochiral ketones

A chiral alcohol and prochiral technology, applied in biofuels, fermentation, organic chemistry, etc., can solve problems such as expensive cofactors and cumbersome recycling

Inactive Publication Date: 2007-03-14
COUNCIL OF SCI & IND RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

During this process, the recovery of the desired product from the emulsion is tedious and requires the occasional use of costly cofactors

Method used

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  • Eco-friendly process for the preparation of chiral alcohols by asymmetric reduction of prochiral ketones
  • Eco-friendly process for the preparation of chiral alcohols by asymmetric reduction of prochiral ketones
  • Eco-friendly process for the preparation of chiral alcohols by asymmetric reduction of prochiral ketones

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 50 g of washed Phaseolus aureus L (mung bean) was put into an Erlenmeyer flask and allowed to soak in deionized water (400 ml) for 24 hours. Add acetophenone I(a) (0.500 g; 0.004 mol) to Phaseolus aureus L (mung bean) soaked in the above water, seal and shake at 15-20° C. for 24 hours. The mung beans were then filtered off and washed with deionized water (3 x 100ml). The combined filtrates were extracted with chloroform (3 x 500ml). The chloroform layer was dried and a crude product (360 mg) was obtained. Pure 1-phenyl-(1S)-1-ethanol II(a) was obtained after silica gel column chromatography using chloroform as eluent.

[0033] Yield: 0.255g, 50%; ee: 84%; ([∝] 25 D = -37.8°, c = 1, methanol)

Embodiment 2

[0035] 50 g of washed Phaseolus aureus L (mung bean) was put into an Erlenmeyer flask and allowed to soak in deionized water (400 ml) for 24 hours. Add 4-chloroacetophenone I(b) (0.500 g; 0.0032 mol) to Phaseolus aureus L (mung bean) soaked in the above water, seal and shake at 15-20° C. for 24 hours. The mung beans were then filtered off and washed with deionized water (3 x 100ml). The combined filtrates were extracted with chloroform (3 x 500ml). The chloroform layer was dried to obtain a crude product (340 mg). After silica gel column chromatography using chloroform as eluent, pure 1-(4-chlorophenyl)-(1S)-1-ethanol II(b) was obtained.

[0036] Yield: 0.253g, 50%; ee: 89.76%; ([∝] 25 D = -38.6°, c = 1, chloroform)

Embodiment 3

[0038] 50 g of washed Phaseolus aureus L (mung bean) was put into an Erlenmeyer flask and allowed to soak in deionized water (400 ml) for 24 hours. Add 4-methylacetophenone I(c) (0.500 g; 0.0037 mol) to Phaseolus aureus L (mung bean) soaked in the above water, seal and shake at 15-20° C. for 24 hours. The mung beans were then filtered off and washed with deionized water (3 x 100ml). The combined filtrates were extracted with chloroform (3 x 500ml). The chloroform layer was dried to obtain a crude product (340 mg). Pure 1-(4-methylphenyl)-(1S)-1-ethanol II(c) was obtained after silica gel column chromatography using chloroform as the eluent.

[0039] Yield: 0.254g, 50%; ee: 94.54%; ([∝] 25 D = -48.5°, c = 1, chloroform)

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Abstract

The present invention relates to a new eco-friendly process for the preparation of chiral alcohols by asymmetric reduction of prochiral ketones in water using soked Phaseolus aureus L (green grams).

Description

field of invention [0001] The present invention relates to a new eco-friendly process for the preparation of chiral alcohols by asymmetric reduction of prochiral ketones in water using soaked Phaseolus aureus L (mung bean). Background of the invention [0002] Chiral alcohols are well-known intermediates that are in good demand as precursors in the development of pharmaceutically important drugs and agrochemicals. The key intermediates can be obtained by resolving the racemate by chemical and biochemical methods. During resolution using racemates, there will always be 50% of the undesired enantiomer present. Therefore, it is important to develop asymmetric synthetic methods that do not generate the undesired enantiomer (50%). Asymmetric reduction of prochiral ketones to single enantiomers is a solution to this problem. [0003] Asymmetric reduction of prochiral ketones by chemical means involves the use of expensive chiral reagents. The biocatalytic method is the most su...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C35/36C07C33/24C12P7/06
CPCY02E50/17Y02E50/10
Inventor 帕尔哈萨拉迪·马利亚蒂库马尔阿斯万·古拉帕利拉梅什·顺卡纳帕利切莫布姆古拉·卡玛拉克什亚马·斯内豪拉塔·奈尔阿伦·坎蒂·达斯
Owner COUNCIL OF SCI & IND RES
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