Method for preparing chiral aryl secondary alcohol

A technology based on secondary alcohols and chirality, which is applied in the field of preparation of aryl alcohols, can solve the problems of cumbersome operation process and unfavorable environment, and achieve the effects of easy catalyst, reduced usage and mild reaction conditions

Inactive Publication Date: 2007-12-12
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But this method has the following disadvantages: first, the first step chemical oxidation reaction is carried out in an organic solvent, which is obviously unfavorable to the environment; secondly, after the first step oxidation reaction is completed, it has to go through precipitation, filtration, washing and distillation separation and purification. The pure product of ketone obtained in the first step is used in the second step of bioreduction, and the whole operation process is relatively cumbersome.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Chemical oxidation of secondary aryl alcohols (1-phenylethanol as an example). Add 1mmol of β-cyclodextrin in 15ml of deionized water, heat to 50-60°C to make it fully dissolved, slowly add 1mmol of methanol solution of 1mmol of racemic 1-phenylethanol, after cooling to room temperature, slowly add 1mmol of NBS, at room temperature Reaction 24h. The conversion of 1-phenylethanol was greater than 99%.

Embodiment 2

[0019] Chemical oxidation of secondary aryl alcohols (1-phenylethanol as an example). Add 0.1mmol β-cyclodextrin to 15ml deionized water, slowly add 1mmol methanol solution of 1mmol racemic 1-phenylethanol, after cooling to room temperature, slowly add 1.2mmol IBX, and react at room temperature for 24h. The conversion of 1-phenylethanol was greater than 99%.

Embodiment 3

[0021] Fermentation of Rhodotorula sp. ECU316-1 CGMCC NO.1735. The medium formula is: glucose 15.0g / L, yeast extract 5.0g / L, peptone 5.0g / L, KH 2 PO 4 1.0g / L, K 2 HPO 4 ·3H 2 O 0.5g / L, NaCl 1.0g / L, MgSO 4 0.5g / L, pH 7.0. Take the Rhodotorula slant strain stored at 4°C, pick a ring and inoculate it into a 250ml shaker flask containing 50ml of culture medium, shake and culture at 160rpm at 30°C for 48h, and harvest the cells by centrifugation. The enzyme activity of the fermentation broth is about 20-40U / L, the cell concentration is about 10-20g (wet weight) / L, and the enzyme activity per unit cell is 2U / g wet cell. The cell viability unit is defined as the amount of cells required to catalyze the reduction of acetophenone to produce 1.0 μmol of 1-phenylethanol per minute under the conditions of 30°C and pH 7.0.

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Abstract

The invention discloses a method for preparing chiral aromatic secondary alcohol. It comprises following steps: a. oxiding racemic aromatic secondary alcohol in beta- cyclodextrin containing water phase into relevant aromatic acetone by using chemical oxidant, reaction time is 6- 24 hours; b. adding reducant additive for reaction for 30 minutes, adding basic substance to moderate pH to 7.0; c. putting the quiescent cell of Rhodotorula sp.)ECU316-1 CGMCC NO.1735 into said solution to catalyze and oxide aromatic acetone into (S)- aromatic secondary alcohol; d. isolating and purifying reaction solution and getting target product. The invention combines chemical and biological method to converse racemic aromatic secondary alcohol to chiral aromatic secondary alcohol with high optical purity (above 99%). It is characterized by temperate reaction condition, simple operation, easy to prepare catalysy and good industrial development prospect.

Description

technical field [0001] The invention relates to a preparation method of aryl alcohol, in particular to a method for preparing chiral aryl secondary alcohol by combining chemistry and biocatalysis. Background technique [0002] Chiral alcohols are an important class of chiral compounds, which can be used as important chiral intermediates and raw materials in the synthesis of pharmaceuticals and fine chemicals. Its synthesis methods can generally be divided into two types: kinetic resolution of racemic alcohols and asymmetric reduction of precursor ketones (including biocatalysis and chemical catalysis methods). Generally, the theoretical yield of kinetic resolution is only 50%, while the method of asymmetric reduction can theoretically obtain optically pure chiral alcohol compounds with 100% yield. But in some cases racemic alcohols are more readily available, while precursor ketones are less readily available and expensive. In this case, using racemic alcohols as target su...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/02C12P1/02C12R1/645
Inventor 徐毅王各许建和张伶娜
Owner EAST CHINA UNIV OF SCI & TECH
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