Synthesis method of alcohol with optical activity

A technology of optical activity and synthesis method, applied in the field of alcohol synthesis, can solve the problems of expensive raw materials, poor reduction effect, low product yield, etc., and achieves the effects of relaxed reaction conditions, reduced input cost of raw materials, and simple operation.

Active Publication Date: 2013-11-27
NANJING OCEAN PHARMA TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Formula I compound is an important receptor antagonist drug Intermediates, the complexity of their synthesis process, and the price of synthetic raw materials directly affect the final drug cost
[0004] In order to reduce the difficulty of drug synthesis process and save the cost of drug synthesis, we have carried out extensive research on the synthesis of compounds of formula I, and found that conventional reducing reagents The reduction effect is poor, and the yield of the product after reduction is low
And using the general reduction reaction operation process, not only the operation process is complicated, but also the raw materials are expensive, which is not suitable for industrialized mass production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Use (S)-CBS-Me, dimethyl sulfide reduction system for reduction.

[0044] Add 42.64g of 2-chloro-1-(3,4-difluorophenyl)ethanone (compound of formula II, molecular weight 190.6; 0.224 mol; 1eq) into a 500ml three-necked flask, add 240ml of anhydrous dichloromethane, stir to dissolve, Nitrogen protection. Cool to -11°C and add 22 mL of S-CBS toluene solution (1M). Add 29 ml of borane dimethyl sulfide (10M) dropwise and finish dropping in about 10 minutes, keeping the temperature below -8°C during the dropping process. Keep at -5~0°C. TLC traced complete disappearance of starting material. Add 25ml of methanol dropwise, 102.5ml of 6% hydrogen peroxide dropwise, and 72ml of 2N sulfuric acid dropwise in order to control the system temperature below 0°C. After dripping, it was raised to room temperature and stirred for 30 min. The layers were separated, the aqueous layer was extracted with 300 ml of dichlorohexane, the organic layers were combined, washed with saturated ...

Embodiment 2

[0047] Use (+)-DIP-Cl reduction system for reduction.

[0048] Add 10 g of 2-chloro-1-(3,4-difluorophenyl)ethanone (the molecular weight of the compound of formula II is 190.6, 0.0524 mol, 1 eq) and THF into the reaction flask, and stir to dissolve. Under nitrogen protection, 41 g (53%) 0.0682 mol of (+)DIP-Cl was added dropwise at 10°C, and the drop was completed in about 10 minutes. Stir at room temperature, and TLC monitors that the reaction of the starting material is complete. After evaporating the system solvent to dryness under reduced pressure, the system weighs 40g, add 50ml of dichloromethane to dissolve, wash with 1mol / L hydrochloric acid 50ml×4 times, spin the organic phase to a dry weight of 30g, add 50ml of methanol to dissolve, wash with 50ml of n-hexane×3 times, and wash with n-hexane The layers were combined and back-extracted with 50 ml of methanol, the methanol layers were combined, and concentrated under reduced pressure to obtain 12 g of an oily substance...

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PUM

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Abstract

The invention relates to the field of chemistry, particularly relates to the field of compound preparation, most particularly relates to a synthesis method of alcohol with optical activity, and aims to find a synthesis method of alcohol with optical activity, which is simple in operation, low in raw material cost, simple in purification process and high in yield, wherein the alcohol is shown as the formula I. According to the invention, a compound II is reduced through (S)-CBS-Me or (+)-DIP-Cl to prepare a compound I, only a reducing agent and corresponding solvent systems are needed, but other catalysts do not need to be added, so that the raw material input cost is reduced; and the requirement for the reaction condition is lower, and harsh conditions such as high temperature, high pressure and the like do not need, so that the synthesis method is suitable for industrial production.

Description

technical field [0001] The invention relates to the field of chemistry, in particular to the field of compound preparation, and more specifically to a method for synthesizing an optically active alcohol. [0002] Background technique [0003] Formula I compound It is an important intermediate of receptor antagonist drugs. The complexity of its synthesis process and the price of synthetic raw materials directly affect the final drug cost. [0004] In order to reduce the difficulty of the drug synthesis process and save the cost of drug synthesis, we have conducted extensive research on the synthesis of the compound of formula I, and found that the reduction effect of the conventional reducing reagent on the compound of formula I is poor, and the yield of the reduced product is low. Moreover, the general reduction reaction operation process is not only complicated in operation and treatment process, but also expensive in raw materials, which is not suitable for industrializ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C33/46C07C29/143
Inventor 陈本顺周长岳江涛
Owner NANJING OCEAN PHARMA TECH
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