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Chiral synthesis method of bepotastine besilate intermediate

A technology of betisine besylate and a synthesis method, applied in the field of chiral synthesis of bepotastine besylate intermediates, can solve the problems of non-industrial production, long steps, low yield and the like, and achieves low production cost, low reaction The effect of stable process and less dosage

Active Publication Date: 2018-03-23
ENANTIOTECH CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Other methods using chiral building blocks have long steps and low yields, and are not industrialized production

Method used

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  • Chiral synthesis method of bepotastine besilate intermediate
  • Chiral synthesis method of bepotastine besilate intermediate
  • Chiral synthesis method of bepotastine besilate intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] In a 5L autoclave, under the condition of connecting argon gas, add 400g of (4-chlorophenyl)(pyridin-2-yl)methanone as a raw material through the feeding port; then add 3L of toluene; Bubble degassing, continuous bubbling for 30min; degassing is complete. Under an argon atmosphere, add 100mg of catalyst (R,R)-DIOPRuCl2(R)-Me-BIMAH through the feeding port, and finally add 6g of potassium tert-butoxide; after the addition, quickly close the feeding port. Replace the argon with hydrogen, slowly introduce hydrogen to 35atm, then close the inflation valve, and close the hydrogen channel; finally stir and keep the reaction at 35°C; the pressure will drop after starting to stir. Observe the pressure change. After 4 hours, the pressure does not change any more. The sample is sent for GC analysis. The conversion rate is 99.7%, and the ee value is 98.2%.

Embodiment 2

[0046] In a 5L autoclave, under the condition of connecting argon gas, add 400g (4-chlorophenyl) (pyridin-2-yl) ketone as a raw material reactant through the feeding port; then add 1L isopropanol and 2L toluene; Inject argon for bubbling degassing, and continue bubbling for 30 minutes; the degassing is completed. Under an argon atmosphere, add 100mg of catalyst (R,R)-DIOPRuCl2(R)-Me-BIMAH through the feeding port, and finally add 6g of potassium tert-butoxide; after the addition, quickly close the feeding port. Replace the argon with hydrogen, slowly introduce hydrogen to 35atm, then close the inflation valve, and close the hydrogen channel; finally stir and keep the reaction at 35°C; the pressure will drop after starting to stir. Observe the change of pressure. After 4 hours, the pressure does not change any more. The sample is sent for GC analysis. The conversion rate is 99.7%, and the ee value is 98.6%.

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Abstract

The invention discloses a chiral synthesis method of a bepotastine besilate intermediate. The chiral synthesis method comprises the following step: by taking (4-chlorphenyl) (pyridine-2-radical) ketone as a raw material, under the action of alkali and a catalyst, carrying out hydrogenation stirring reaction in a solvent, so as to obtain (S)-(4-chlorphenyl) (pyridine-2-radical) methanol. Accordingto the method disclosed by the invention, a high-purity product can be obtained only by one-step catalytic hydrogenation reaction of a production process, so that the process period is greatly shortened; the chiral synthesis method has the characteristics of simple synthesis line, small use amount of the catalyst, stable reaction process, environmental friendliness, economy and the like, and has an extremely industrial application value in the aspect production and preparation of the (S)-(4-chlorphenyl) (pyridine-2-radical) methanol.

Description

technical field [0001] The invention belongs to the field of synthesis of pharmaceutical and chemical intermediates, and mainly relates to a chiral synthesis method of a bepotastine benzenesulfonate intermediate. Background technique [0002] Bepotastine besilate, the chemical name is 4-[4-[(S)-[(4-chlorophenyl)pyridin-2-yl]methoxy]piperidin-1-yl] Butyric acid monosulfonate is an antiallergic drug developed by Ube Industries of Japan. It was first launched in Japan in 2000 under the trade name Talion. Histamine H 1 The receptor antagonist can be used to treat allergic diseases such as allergic rhinitis, has rapid action, high selectivity, no sedative adverse reaction caused by previous antiallergic drugs, and good curative effect. Bepotastine besilate can also inhibit the infiltration of eosinophils caused by antigens and reduce allergic inflammation. [0003] [0004] Bepotastine benzenesulfonate, its chiral structure is mainly composed of the intermediate of (S)-(4-c...

Claims

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Application Information

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IPC IPC(8): C07D213/30
CPCC07D213/30
Inventor 徐亮毛波李彦雄
Owner ENANTIOTECH CORP
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