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Synthesis method of 3-aminopyrrolidine dihydrochloride

A technology of aminopyrrolidine dihydrochloride and aminopyrrolidine, which is applied in the field of synthesis of 3-aminopyrrolidine dihydrochloride, and can solve problems such as many steps, long reaction routes, and low yields

Pending Publication Date: 2022-04-19
赤峰万泽药业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the synthetic routes disclosed in Japan, there are the following problems: 1. The reaction route is long, with many steps, the total yield is low, and the pollution is large; 2. Some reaction routes involve oxime formation reactions, resulting in lower yields; 3. The reaction conditions during debenzylation are harsh, high temperature and high pressure are not easy to control; the industrial production cost of 3-aminopyrrolidine is too high
[0006] Chinese patent application CN2006101501116 discloses a synthetic method for preparing 3-aminopyrrolidine using benzylamine, ethyl acrylate, and ethyl chloroacetate as main starting materials through addition, cyclization, hydrolysis, and hydrogenation (two steps). ; avoid the generation of oxime intermediates, and improve the yield relative to the method disclosed in Japan, and obtain a new synthesis method with simple technology and low cost; but due to the high reactivity of raw materials, although the yield increases, the yield of the product The yield is unstable, and the by-products 3-hydroxypyrrolidinol, 4-aminopiperidine, and 3-methylaminopyrrolidine appear, and the output of by-products is unstable; the purity of the product is improved by distillation and purification of organic solvents, which increases the synthesis cost

Method used

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  • Synthesis method of 3-aminopyrrolidine dihydrochloride
  • Synthesis method of 3-aminopyrrolidine dihydrochloride
  • Synthesis method of 3-aminopyrrolidine dihydrochloride

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Embodiment 1

[0073] This embodiment provides a method for synthesizing 3-aminopyrrolidine dihydrochloride, comprising the following steps:

[0074] 1) Preparation of benzyl-(3-ethoxy-3-enyl)-(1-vinylethoxymethyl)amine liquid;

[0075] (1) Use a vacuum pump to sequentially draw toluene (recoverable for mechanical use) and benzylamine into the reaction tank; the interlayer passes through cooling water or cold brine;

[0076] (2) Under stirring, the ethyl acrylate is sucked into the reaction tank in stages, and after the feeding is completed, the temperature is naturally raised to be stable, and the stirring is continued for 10-15 hours;

[0077] (3) Within 40°C, fill in 79.0kg of hydrogen chloride, after the feeding is completed, continue to stir and react for 4-6 hours;

[0078] (4) Open centrifuge, centrifugal separation; Filter cake is washed with toluene; All filtrates are merged into retort; Inhale ethyl chloroacetate, triethylamine;

[0079] (5) After the pumping is completed, the te...

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Abstract

The invention discloses a synthetic method of 3-aminopyrrolidine dihydrochloride. The synthetic method comprises the following steps: preparing benzyl-(3-ethoxy-3-alkenyl)-(1-vinyl ethoxy methyl) amine liquid; preparation of a 1-benzyl-3-pyrrolidone solution; preparation of a 1-benzyl-3-aminopyrrolidine solution; preparing a 1-benzyl-3-aminopyrrolidine salt; preparing a 3-aminopyrrolidine solution; the yield and purity of the 3-aminopyrrolidine dihydrochloride are improved by controlling the activity of the reaction main materials of each part in a segmented manner and carrying out a directional hydrogenation manner.

Description

technical field [0001] The invention relates to a synthesis method of 3-aminopyrrolidine dihydrochloride. Background technique [0002] 3-aminopyrrolidine dihydrochloride and its optical isomers are key intermediates in the synthesis of a large number of drugs. The optically active 3-aminopyrrole dihydrochloride is a key intermediate for the preparation of agricultural chemicals such as vinylpyrrolidone-cephalosporin derivatives and pharmaceutical active substances tosufloxacin and other quinolone antibacterial drugs. [0003] Japanese patent application JP61057579A reports: N-ethoxycarbonylglycine ethyl ester is first added to ethyl acrylate, followed by Dieckmann ring closure, followed by selective hydrolysis and decarboxylation to obtain pyrrolidone. In 3-aminopyrrolidine. [0004] Japanese open patent JP3133954A reports: N-benzylglycine ethyl ester first adds ethyl acrylate, then carries out Dieckmann ring synthesis under the presence of t-BuOK to obtain N-benzyl-4-for...

Claims

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Application Information

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IPC IPC(8): C07D207/14
CPCC07D207/14
Inventor 张海立郭振军刘海涛
Owner 赤峰万泽药业股份有限公司
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