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Process for synthesizing pregabalin

A synthesis process, the technology of pregabalin, which is applied in the field of synthesis process of pregabalin, can solve the problems of harsh conditions, low total yield, high cost, etc., and achieve the effect of less reaction steps, increased total yield and mild process conditions

Inactive Publication Date: 2015-12-09
CHENGDU AIBIKE BIOTECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

One of the current synthetic techniques is asymmetric synthesis of (+)-norephedrine as a chiral auxiliary agent, the conditions are harsh and the cost is high; the second synthetic technique uses diethyl malonate and isovaleraldehyde as starting materials , requires the use of highly toxic potassium cyanide; the third synthesis process uses isovaleraldehyde, cyanoacetamide or ethyl cyanoacetate as raw materials, passes through the intermediate 3-isobutylglutaric acid, and finally obtains the target product, and the route is longer , the operation is complicated, and its process has been improved, but the total yield is low, only 61%

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Synthesis of 5-methyl-2-hexenoic acid: Dissolve 30g of malonic acid in 50ml of anhydrous pyridine, cool to 0°C in an ice-salt water bath, slowly add 28ml of freshly steamed isovaleraldehyde to the above solution under vigorous stirring In 30 minutes, the dropwise addition was completed, and a yellow slurry was formed. The ice-brine bath was removed, and the reaction mixture was allowed to warm to room temperature naturally, and stirring was continued for 12 h, and the reaction was monitored by TLC. The reaction mixture turned into a colorless clear solution, heated to 60°C, kept for 5h, CO2 gas was released slowly, raised to 90°C, continued for 2h, after the release of CO2 was completed, the reaction mixture was poured into 100ml of water, and the upper organic phase was separated , Dissolved in 100ml ethyl acetate. The organic phase was washed with 140ml of 6.0mol / l hydrochloric acid solution and 100ml of water, and dried with anhydrous sodium sulfate. Ethyl acetate ...

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PUM

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Abstract

The invention discloses a process for synthesizing pregabalin. According to a synthesis route in the process, isovaleraldehyde and propane diacid are condensed for esterification; under the catalytic action of tetramethyl guanidine, a Michael addition is performed with nitromethane; a palladium-carbon catalyst of which the mass fraction is 10% is adopted in glacial acetic acid for reduction and hydrogenation; a raceme (+ / -)-1 is obtained by directly performing hydrolysis in a hydrochloric acid solution without separation, and can be split to obtain (S)-1. The process provided by the invention is available, a few of reaction steps are taken, process conditions are mild, and the total yield is greatly improved on the basis of the prior art.

Description

Technical field [0001] The invention is involved in the field of process technology, which specifically refers to a Pedibarin's synthesis process. Background technique [0002] Progabalin [Pregabalin, (s).1] Chemical name (s) 1 3_ ammonia methyl-based one 孓 甲 己 己 [[(3S) -3 one aminomethyl-5 one Methylhex -noicAcid] is an amino p-binoche acid (GABA) developed by the US Pfizer Company (GABA)The receptor antagonist has been approved by the European Union in July 2004 and was listed for the first time in the UK for the first time for patients with epilepsy for patients with epilepsy.Compared with Gabapentin, which is clinically used, this product has a stronger anticonia, smaller adverse reactions, has the advantages of low dosage, small number of times, and anti -anxiety.Essence [0003] Proven is a handicap, and its S -shaped isomer has pharmacological activity.One of the current synthetic processes is (+) one -to -be, one -to -alive synthesis for handicides, harsh conditions and h...

Claims

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Application Information

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IPC IPC(8): C07C229/08C07C227/20
Inventor 何金蓉
Owner CHENGDU AIBIKE BIOTECH
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