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The preparation method of 4-amino-2-cyclopentene-1-methanol hydrochloride

A technology of hydrochloride and cyclopentene, applied in the field of preparation of 4-amino-2-cyclopentene-1-methanol hydrochloride, can solve the problems of high pollution, high cost, and low price of reaction raw materials, and achieve Low price, avoid contact and reaction, reduce cost and pollution effect

Active Publication Date: 2021-03-19
安徽红杉生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of this application is to provide a preparation method of 4-amino-2-cyclopentene-1-methanol hydrochloride, the price of the reaction raw materials is low, and can effectively solve the problem of using a large amount of high-cost, high-pollution acid catalysts question

Method used

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  • The preparation method of 4-amino-2-cyclopentene-1-methanol hydrochloride
  • The preparation method of 4-amino-2-cyclopentene-1-methanol hydrochloride
  • The preparation method of 4-amino-2-cyclopentene-1-methanol hydrochloride

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preparation example Construction

[0016] The embodiment of the present application provides a preparation method of 4-amino-2-cyclopentene-1-methanol hydrochloride, comprising: 2-azabicyclo[2,2,1]hept-5-ene-3- The ketone undergoes esterification and ring-opening reaction in the presence of thionyl chloride to obtain the ring-opening compound hydrochloride; the ring-opening compound hydrochloride is subjected to reduction treatment in an aqueous solution of dichloromethane to obtain 4-amino-2 - A reaction solution of cyclopentene-1-methanol hydrochloride.

[0017] In the examples of the present application, 2-azabicyclo[2,2,1]hept-5-en-3-one was esterified and ring-opened in the presence of thionyl chloride to obtain A structurally stable ring-opened compound that exists in the form of a salt. The ring-opening compound hydrochloride is reduced in an aqueous solution of dichloromethane. During the reduction process, the organic amine is effectively dissociated into the dichloromethane and the ester group is dis...

Embodiment 1

[0038] A preparation method of (1S,4R)-4-amino-2-cyclopentene-1-methanol hydrochloride, comprising:

[0039] S1. Add 50g of (1R,4S)-2-azabicyclo[2,2,1]hept-5-en-3-one and 100g of absolute ethanol in the flask, and cool down to 0°C while stirring. Then, 60 g of thionyl chloride was added dropwise to the system, and the temperature of the system was controlled to be less than 10° C. during the dropwise addition. After the addition of thionyl chloride was completed, the system was heated to 30°C and stirred for 1 hour. After the reaction, the (1S,4R)-(-)ethyl-4-aminocyclopent-2-ene-1-carboxylate obtained The salt hydrochloride is concentrated and dried for later use.

[0040] S2. (1S,4R)-(-)ethyl-4-aminocyclopent-2-ene-1-carboxylate hydrochloride obtained in S1 was dissolved in 200mL water and 200mL dichloromethane mixed to obtain the dichloromethane In the aqueous solution of methyl chloride, stir to dissolve and clarify and cool down to below 10°C to obtain a mixed solution; ...

Embodiment 2

[0043] A preparation method of (1S,4R)-4-amino-2-cyclopentene-1-methanol hydrochloride, comprising:

[0044] S1. Add 50g of (1R,4S)-2-azabicyclo[2,2,1]hept-5-en-3-one and 100g of absolute ethanol in the flask, and cool down to 0°C while stirring. Then, 60 g of thionyl chloride was added dropwise to the system, and the temperature of the system was controlled to be less than 10° C. during the dropwise addition. After the addition of thionyl chloride was completed, the system was heated to 30°C and stirred for 1 hour. After the reaction, the (1S,4R)-(-)ethyl-4-aminocyclopent-2-ene-1-carboxylate obtained The salt hydrochloride is concentrated and dried for later use.

[0045] S2. (1S,4R)-(-)ethyl-4-aminocyclopent-2-ene-1-carboxylate hydrochloride obtained in S1 was dissolved in 175mL water and 205mL dichloromethane mixed to obtain dichloromethane In the aqueous solution of methyl chloride, stir to dissolve and clarify and cool down to below 10°C to obtain a mixed solution; add ...

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Abstract

The invention provides a preparation method of 4-amino-2-cyclopentene-1-methanol hydrochloride, which belongs to the technical field of synthesis of medical intermediates. The preparation method of the 4-amino-2-cyclopentene-1-methanol hydrochloride comprises the following steps: carrying out an esterification ring-opening reaction on 2-azabicyclo [2, 2, 1]hept-5-ene-3-ketone in the presence of thionyl chloride so as to obtain a ring-opening compound hydrochloride; carrying out reduction treatment on the ring-opening compound hydrochloride in an aqueous solution of dichloromethane to obtain areaction solution containing 4-amino-2-cyclopentene-1-methanol hydrochloride. The price of reaction raw materials is low, and the problem that a large amount of high-cost and high-pollution acid catalysts need to be used can be effectively solved.

Description

[0001] This application claims the priority of the Chinese patent application (2020103752513) submitted on April 30, 2020, which is incorporated herein by reference in its entirety. technical field [0002] The present application relates to the technical field of synthesis of pharmaceutical intermediates, in particular to a preparation method of 4-amino-2-cyclopentene-1-methanol hydrochloride. Background technique [0003] 4-Amino-2-cyclopentene-1-methanol hydrochloride is a commonly used pharmaceutical intermediate, in which (1S,4R)-4-amino-2-cyclopentene-1-methanol hydrochloride is used as The key intermediate used to prepare anti-AIDS drugs such as abacavir and carbavir has important application value. [0004] In the prior art, 2-azabicyclo[2,2,1]hept-5-en-3-one is usually used in the synthesis process of 4-amino-2-cyclopentene-1-methanol hydrochloride to develop Cyclic esterification, followed by amino protection with BOC anhydride, followed by reduction, deprotection...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C213/00C07C213/10C07C215/42C07C227/22C07C229/48
CPCC07C213/00C07C213/10C07C227/22C07C2601/10C07C229/48C07C215/42
Inventor 高仰哲吴法浩李钢王志航
Owner 安徽红杉生物医药科技有限公司
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