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Method for synthesizing optically pure (R)-3-carbamoymethyl-5-methylhexanoic acid

A technology of carbamoylmethyl and methylhexanoic acid, which is applied in the field of synthesis of optically pure 3-carbamoylmethyl-5-methylhexanoic acid, can solve the problem of high toxicity of resolving agents, high raw material prices, Slow reaction speed and other problems, to achieve the effect of shortening the reaction time, low raw material cost and fast reaction speed

Pending Publication Date: 2019-08-23
EASTSKY PHARM ANHUI TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there are still problems in the domestic preparation of 3-aminomethyl-5-methylhexanoic acid: slow reaction speed, high raw material price, low conversion rate, high toxicity of resolving agent, etc.

Method used

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  • Method for synthesizing optically pure (R)-3-carbamoymethyl-5-methylhexanoic acid

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Effect test

Embodiment 1

[0022] A kind of synthetic method of optically pure (R)-3-carbamoylmethyl-5-methylhexanoic acid of the present invention comprises the following steps:

[0023] Step 1: Add 56.5g (0.5mol) of ethyl cyanoacetate and 100ml of n-hexane into a 500ml reaction flask, stir evenly and control the temperature range at 0-5°C, then slowly add 0.5g of triethylenediamine and iso 43g (0.5mol) of valeraldehyde, the color of the solution gradually becomes light yellow, stir at room temperature, and then heat up to 90-100°C, use a water separator to reflux and separate water, react until no water comes out, cool down; concentrate under reduced pressure, Obtain ethyl 2-cyano-5-methyl-2-ene hexanoate;

[0024] Step 2, directly add 72.2g (0.5mol) of diethyl malonate and 5g of triethylenediamine to the product obtained in step 1, stir and react for 10 hours, directly add 500ml of hydrochloric acid, heat to reflux until the reaction is completed, and cool to room temperature Extract and concentrate...

Embodiment 2

[0029] Step 1: Add 56.5g (0.5mol) of ethyl cyanoacetate and 100ml of n-hexane into a 500ml reaction flask, stir evenly and control the temperature range at 0-5°C, then slowly add 0.5g of triethylenediamine and iso 43g (0.5mol) of valeraldehyde, the color of the solution gradually becomes light yellow, stir at room temperature, and then heat up to 90-100°C, use a water separator to reflux and separate water, react until no water comes out, cool down; concentrate under reduced pressure, Obtain ethyl 2-cyano-5-methyl-2-ene hexanoate;

[0030] Step 2, directly add 72.2g (0.5mol) of diethyl malonate and 5g of triethylenediamine to the product obtained in step 1, stir and react for 10 hours, directly add 500ml of hydrochloric acid, heat to reflux until the reaction is completed, and cool to room temperature Extracted twice with dichloromethane, concentrated under reduced pressure to obtain 3-isobutyl-2-cyano-4-ethoxycarbonyl-glutaric acid ethyl ester;

[0031] Combine the extracted...

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Abstract

The invention relates to the technical field of fine chemical engineering production and in particular discloses a method for synthesizing optically pure (R)-3-carbamoymethyl-5-methylhexanoic acid. The method comprises the following steps: 1, synthesizing 2-cyano-5-methyl-2-ene ethyl hexanoate; 2, synthesizing 3-isobutyl-2-cyano-4-ethoxycarbonyl-ethyl glutarate; 3, synthesizing 3-isobutylglutaricanhydride; 4, synthesizing (+ / -)-3-carbamoymethyl-5-methylhexanoic acid; and 5, synthesizing the (R)-3-carbamoymethyl-5-methylhexanoic acid. According to the method disclosed by the invention, the defects in the prior art are overcome, and the provided synthetic method is low in raw material cost, high in reaction speed, simple and feasible, is suitable for large-scale industrial production and has very high economic benefits.

Description

technical field [0001] The invention relates to the technical field of fine chemical production, in particular to a method for synthesizing optically pure (R)-3-carbamoylmethyl-5-methylhexanoic acid. Background technique [0002] Pregabalin (PGB) is a new type of γ-aminobutyric acid receptor blocker developed by Pfizer, and has become one of the more efficient, safe and convenient drugs for the treatment of neuralgia; 3-aminomethyl- 5-methylhexanoic acid is a key intermediate for the preparation of pregabalin. [0003] At present, the domestic process for preparing 3-aminomethyl-5-methylhexanoic acid still has problems such as slow reaction speed, high raw material price, low conversion rate, and high toxicity of resolving agent. Contents of the invention [0004] The purpose of this invention is to provide a kind of synthetic method of optically pure (R)-3-carbamoylmethyl-5-methylhexanoic acid, overcome the deficiencies in the prior art, provide a kind of raw material co...

Claims

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Application Information

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IPC IPC(8): C07D309/32C07C231/10C07C231/20C07C233/05C07B57/00
CPCC07C253/30C07C51/09C07C51/38C07D309/32C07C231/10C07C231/20C07B57/00C07B2200/07C07C255/23C07C255/19C07C55/02C07C233/05
Inventor 刘耀鹏于振云周中味万庆卢俊付雪莲
Owner EASTSKY PHARM ANHUI TECH
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