Method for preparing chiral secondary alcohol

A secondary alcohol, chiral technology, applied in the field of preparation of chiral alcohol by hydrolysis, to achieve the effect of simple reaction operation process, low price and low catalyst toxicity

Active Publication Date: 2013-04-17
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the process of preparing chiral secondary alcohols, in order to solve the catalyst needs to meet the simple and easy to manufacture, low cost, low toxicity, environmental protection, large natural abundance, relatively stable catalytic system, high catalytic activity and chiral induction effect , while avoiding high temperature, high pressure and ultra-low temperature reactions, reducing the cost and energy consumption in the reaction process, and requiring low requirements for reaction conditions and equipment, the present invention proposes a method for preparing chiral secondary alcohols. Mild conditions, low equipment requirements, low energy consumption, high chemical and optical yield, etc.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] At room temperature, in a reactor equipped with a magnetic stirrer, add R, R -chiral furimine (0.025mol), tetrahydrofuran (1500ml), zinc acetate (0.025mol), then add acetophenone (0.5mol), stir for 10 min, then add HSi(OEt) 3 (1.0 mol), reacted for 48 hours, and ended the reaction. The reactant was carefully poured into a KOH (187 g) solution with a mass percentage concentration of 15%, hydrolyzed for 180 min, and the standing solution was divided into an organic phase and an aqueous phase. The organic phase Fractions were collected by distillation under reduced pressure to obtain 58 g of 1-phenylethanol, with a yield of 96% and an optical purity of 65%. ee .

Embodiment 2

[0025] At room temperature, in a reactor equipped with a magnetic stirrer, add S, S -chiral furimine (0.025mol), tetrahydrofuran (1500ml), zinc acetate (0.025mol), then add acetophenone (0.5mol), stir for 10 min, then add HSi(OEt) 3 (1.0 mol), reacted for 48 hours, and ended the reaction. The reactant was carefully poured into a KOH (187 g) solution with a mass percentage concentration of 15%, hydrolyzed for 180 min, and the standing solution was divided into an organic phase and an aqueous phase. The organic phase Fractions were collected by distillation under reduced pressure to obtain 56 g of 1-phenylethanol with a yield of 93% and an optical purity of 62% ee .

Embodiment 3

[0027] At room temperature, in a reactor equipped with a magnetic stirrer, add R, R -Chiral furimine (0.1mol), tetrahydrofuran (1500ml), zinc acetate (0.05mol), then add p-chloroacetophenone (0.5mol), stir for 10 min, then add HSi(OCH 3 ) 3 (1.5 mol), reacted for 72 hours, ended the reaction, and the reactant was carefully poured into a solution of hydrochloric acid (120g) with a mass percent concentration of 15%, hydrolyzed for 150 min, and the standing solution was divided into an organic phase and an aqueous phase, and the organic phase was passed through Fractions were collected by distillation under reduced pressure to obtain 62.0 g of 1-naphthyl ethanol, with a yield of 80% and an optical purity of 54% ee .

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Abstract

The invention relates to the field of organic chemistry. In a process of preparing a chiral secondary alcohol, the invention provides a method for preparing the chiral secondary alcohol to meet the requirements of a catalyst of simplicity and easiness of manufacturing, low cost, low toxin, environmental friendliness, great natural abundance, more stable catalyzing system, very high catalytic activity and chiral induction effect, capability of avoiding high-temperature and high-pressure and ultralow-temperature reactions, cost reduction and energy consumption reduction in a reaction process, and low requirements on reaction conditions and equipment requirements. The method takes prochiral ketone and hydrogen-containing silane as raw materials and takes a complex formed by taking zinc acetate and chiral furamide to react as a catalyst; and the materials are reacted at a normal temperature and are hydrolyzed to obtain the chiral secondary alcohol. The method has a series of characteristics of moderate reaction conditions, low equipment requirements, low energy consumption, high chemical and optical yield and the like.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a method for asymmetrically catalyzing the hydrosilylation of latent chiral ketones at room temperature, and then hydrolyzing them into chiral alcohols. Background technique [0002] Fine chemical chemistry and the synthesis of pharmaceutical intermediates are a pillar industry of my country's new national economy and a sunrise industry with sustainable development. Among them, the research and development of drugs and the synthesis of new chemicals play a very important role in the long-term development of the country. important role. Among them, the development and production of chiral drugs is the top priority, which is of positive significance to the advancement and practice of scientific development, and chiral secondary alcohols are an indispensable raw material for the synthesis of pharmaceutical intermediates and drug research and development , has extremely wide appl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/09C07C33/22C07C33/46C07C41/26C07C43/23B01J31/22
Inventor 来国桥庞少峰彭家建白赢厉嘉云肖文军
Owner HANGZHOU NORMAL UNIVERSITY
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