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Optically pure Sibutramine and process for preparing salt derivative thereof

A preparation process and optical technology, applied in the field of preparation process of optically pure sibutramine and its derivative salts, can solve the problems of inability to form sibutramine resolution process, non-reproducibility, and low resolution efficiency , to achieve the effect of high splitting efficiency, convenient preparation, and improved splitting efficiency

Inactive Publication Date: 2009-08-26
广州市金匮贸易有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the cost of the resolving agent used in this method is relatively high, and the resolution efficiency is not high
Although the resolution method is very suitable for the industrial production of optically pure sibutramine, the two methods reported so far do not have good reproducibility and cannot form an effective sibutramine resolution process

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Weigh 2.1 g of sibutramine racemate and put it into a 250 mL round bottom bottle and dissolve it in 100 mL of ethyl acetate, add 3.22 g of O, O'-di-o-chlorobenzoyl-L-tartaric acid resolving agent, stir, and heat Reflux and stir for half an hour, the crystals gradually dissolve and the solution becomes transparent. After standing or stirring to cool to room temperature, filter and dry the filter cake to obtain 2.3 g of white powdery crystals-O, O'-di-o-chlorobenzoyl-L-tartrate of dexsibutramine. The optical purity was 86.25% e.e., and the yield was 43.98%.

Embodiment 2

[0030] Weigh 2.1 g of sibutramine racemate and put it into a 50 mL round bottom bottle, dissolve it in 20 mL of 1,2-dichloroethane, add 3.22 g of O, O'-di-o-chlorobenzoyl-L-tartaric acid Dispensing and stirring, heated to reflux and stirred for half an hour, the crystals gradually dissolved and the solution became transparent. After standing or stirring to cool to room temperature, filter, and dry the filter cake to obtain 2.0 g of white powdery crystals-O, O'-di-o-chlorobenzoyl-L-tartrate of dexsibutramine. The optical purity was 80.29% e.e., and the yield was 38.28%.

Embodiment 3

[0032] Weigh 2.1 g of sibutramine racemate and put it into a 500 mL round bottom bottle and dissolve it in 120 mL of acetone, add 3.38 g of O, O'-di-p-nitrobenzoyl-L-tartaric acid resolving agent and stir, the crystals gradually dissolved and the solution became transparent. Add 120mL of n-hexane, heat the solution to reflux and stir for half an hour after the solution becomes mixed, let it stand to cool to room temperature, filter, and dry the filter cake to obtain 2.25 g of white powder crystals - O, O'-dip-nitrate of dexsibutramine benzoyl-L-tartrate. The optical purity was 90.09% e.e., and the yield was 43.02%.

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Abstract

The invention discloses a preparation process of optically pure Sibutramine. In the process, chiral O,O'-diaryl formacyl tartaric acid is taken as a resolving agent to resolve Sibutramine raceme to obtain diastereomer salt thereof; and the diastereomer salt is separated, alkalized and extracted to obtain optically pure levorotatory Sibutramine or optically pure dextrorotatory Sibutramine. The invention further discloses a preparation process of a salt derivative of the optically pure Sibutramine, and the optically pure Sibutramine obtained by the process is combined with an acid compound to form the salt derivative of the optically pure Sibutramine. The preparation process of the optically pure Sibutramine is characterized by high resolving efficiency, simple and practical process, short resolving cycle and the like; and the used resolving agent can be recovered and recycled. Furthermore, the salt derivative of the optically pure Sibutramine prepared by the invention can expand Sibutramine application scope.

Description

technical field [0001] The invention relates to a preparation process of optically pure sibutramine and its derivative salt, belonging to the field of organic synthesis. Background technique [0002] Sibutramine, the chemical name is N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-N,N'-dimethylamine, there is a Chiral carbon atoms are the main components of the new weight-loss drug Qumei. Sibutramine hydrochloride is a new type of weight-loss drug researched and developed by Knoll Pharmaceutical Company of the United States. It has the characteristics of good absorption and definite curative effect. After sibutramine hydrochloride went on the market, about 10 million people have used this product successively, and the sales volume has also increased at an annual growth rate of 50%. It has become the best-selling weight-loss drug popular in Europe and America. However, the drug is currently used clinically in the form of a racemate, and no chiral sibutramine hydrochlorid...

Claims

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Application Information

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IPC IPC(8): C07C211/29C07C209/88C07C209/68
CPCC07C209/68C07B2200/07C07C209/88C07C2101/04C07C2601/04
Inventor 胡昱孙晓霞郭瑛周志真陈红卫杨金诚
Owner 广州市金匮贸易有限公司
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