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Synthetic method of tapentadol

A synthetic method, the technology of tapentadol, applied in the field of drug synthesis, can solve the problems of complex reaction route, no one-step ammoniation, complicated post-treatment, etc., and achieve the effect of simplifying the reaction route, reducing production cost and reducing post-processing steps

Active Publication Date: 2014-05-14
暨明医药科技(苏州)有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the above synthetic route uses oxazolidinone as a chiral prosthetic group, which is more expensive, and the second and third step reaction routes are complicated, and there is no one-step ammoniation, and the post-treatment is complicated

Method used

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  • Synthetic method of tapentadol
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  • Synthetic method of tapentadol

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Embodiment

[0038] This embodiment provides a synthesis method of tapentadol, the method comprising the following steps: using meta-substituted cinnamic acid as a starting material, reacting with a chiral prosthetic group to obtain an amide; Reaction, two chiral centers are introduced to obtain a chiral product; the chiral product is reduced and deprotected to obtain a chiral alcohol; the chiral alcohol is subjected to amination reaction and substitution reaction to obtain tapentadol.

[0039] The method includes the following processes:

[0040]

[0041] Specifically, the method includes the following steps:

[0042] Step 1, using m-methoxycinnamic acid (compound A, R=Me, 1 times the amount) as the starting material, dissolved in dichloromethane (10 times the amount), cooled to 0 degrees, and added triethylamine (3 times the amount), slowly drop pivaloyl chloride (1 times the amount). After stirring for 3 hours, (1R,2R)-pseudoephedrine (1 times the amount) was added, and stirred ove...

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Abstract

The invention discloses a synthetic method of tapentadol. The method comprises the following steps: reacting meta-substitution cinnamic acid serving as a starting material with a chiral adjuvant to obtain amide; reacting the amide with a nucleophilic reagent and an electrophilic reagent, and introducing two chiral centers to obtain a chiral product; performing reduction and deprotection on the chiral product to obtain chiral alcohol; performing an amination reaction and a substitution reaction on the chiral alcohol to obtain the tapentadol. The tapentadol is synthesized by taking cheap and readily-available (1R,2R)-psedo-ephedrine as the chiral adjuvant, forming two chiral centers by using a one-pot method and performing simper deprotection and subsequent transformation. By adopting the synthetic method, the reaction route can be simplified, post-treatment steps can be reduced, and the production cost is reduced. The synthetic method is more suitable for industrial application.

Description

technical field [0001] The invention relates to a synthesis method of tapentadol, which belongs to the field of drug synthesis. Background technique [0002] Tapentadol, chemical name (-)-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol (English name (-)-( 1R,2R)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)phenol), is a new type of central analgesic with a dual mechanism of action developed by the German Grünenthal Pharmaceutical Company and Johnson&Johnson Company. On November 21, 2008, it was approved for marketing by the US FDA. Studies have shown that tapentadol has good effects on acute, inflammatory, and chronic neuropathic pain, and can obtain satisfactory blood drug levels through intravenous or oral administration, and is less likely to produce analgesic tolerance and physical dependence than morphine, and compared with Other drugs with equivalent analgesic doses have fewer side effects and have good prospects in the treatment of acute and chronic moderate ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C215/54C07C213/00
Inventor 李斌峰陈剑戈孙涛
Owner 暨明医药科技(苏州)有限公司
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