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A kind of preparation method of tert-butyl 1-hydroxyl-8-azaspirane[4,5]decane-8-carboxylate

A technology of azaspiro and tert-butyl, which is applied in the field of preparation of tert-butyl 1-hydroxy-8-azaspiro[4,5]decane-8-carboxylate, can solve the problem of not being suitable for industrialization Synthetic method and other problems, to achieve the effect of short synthetic route, easy reaction and convenient operation

Active Publication Date: 2018-03-27
WUXI APPTEC (TIANJIN) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Mainly solve the technical problem that there is no suitable industrial synthesis method at present

Method used

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  • A kind of preparation method of tert-butyl 1-hydroxyl-8-azaspirane[4,5]decane-8-carboxylate

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Embodiment 1

[0010] Example 1: a. Compound 1 (40 g, 0.12 mol) was added into 6M hydrochloric acid (500 mL), the reaction solution was heated to reflux, and the reaction was continued for 10-20 hours. TLC (petroleum ether / ethyl acetate volume ratio=1 / 1) showed that the reaction was complete. The reaction system was cooled to room temperature and distilled under reduced pressure to obtain compound 2 (23.3 g) as a gray solid with a yield of 99.8%.

[0011] b. Dissolve compound 2 (23.3 g, 0.12 mol) and sodium carbonate (19.5 g, 0.18 mol) in a mixed solution of dioxane and water (1 / 1,500 mL). Control the reaction temperature at 10-20°C, slowly add di-tert-butyl carbonate (28 g, 0.13 mol) in batches. The reaction was controlled to continue the reaction at room temperature for 10-20 hours. TLC (petroleum ether / ethyl acetate volume ratio=2 / 1) showed that the reaction was complete. The reaction solution was distilled under reduced pressure to remove dioxane. The residue was extracted with ethyl...

Embodiment 2

[0015] Example 2: a. Compound 1 (400 g, 1.23 mol) was added into 6M hydrochloric acid (1.5 L), the reaction solution was heated to reflux, and the reaction was continued for 10-20 hours. TLC (petroleum ether / ethyl acetate volume ratio=1 / 1) showed that the reaction was complete. The reaction system was cooled to room temperature and distilled under reduced pressure to obtain compound 2 (233 g) as a gray solid with a yield of 99.8%.

[0016] b. Dissolve compound 2 (233 g, 1.23 mol) and sodium carbonate (195 g, 1.84 mol) in a mixed solution of dioxane and water (1 / 1, 1 L). Control the reaction temperature at 10-20°C, slowly add di-tert-butyl dicarbonate (281 g, 1.29 mol) in batches. The reaction was controlled to continue the reaction at room temperature for 10-20 hours. TLC (petroleum ether / ethyl acetate volume ratio=2 / 1) showed that the reaction was complete. The reaction solution was distilled under reduced pressure to remove dioxane. The residue was extracted with ethyl a...

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Abstract

The invention relates to a preparation method of tertiary butyl 1-hydroxyl-8-azaspirane[4,5]decane-8-carboxylic ester and mainly solves the technical problems that a method suitable for industrial synthesis does not exist at present. The preparation method comprises three steps: firstly, generating a compound 2 by a compound 1 under the action of hydrochloric acid; secondly, obtaining a compound 3 by enabling the compound 2 to react with di-tert-butyl dicarbonate in a mixed solution of dioxane and water under the existence of sodium carbonate; finally, obtaining a product 4 by treating the compound 3 through sodium borohydride, wherein a reaction formula is as shown in the description. The tertiary butyl 1-hydroxyl-8-azaspirane[4,5]decane-8-carboxylic ester obtained through the preparation method disclosed by the invention is a useful intermediate or a product compounded by many medicines.

Description

technical field [0001] The present invention relates to a synthesis method of tert-butyl 1-hydroxyl-8-azaspirane[4,5]decane-8-carboxylate (CAS: 1357352-29-4). Background technique [0002] tert-butyl 1-hydroxy-8-azaspirane[4,5]decane-8-carboxylate and related derivatives are widely used in medicinal chemistry and organic synthesis. At present, there are few reports on the synthesis of tert-butyl 1-hydroxy-8-azaspirane[4,5]decane-8-carboxylate, and similar literature reactions are dangerous and have long routes and low yields . Therefore, it is necessary to develop a synthetic method with easy-to-obtain raw materials, convenient operation, easy-to-control reaction and suitable overall yield. Contents of the invention [0003] The purpose of the present invention is to develop a kind of tert-butyl 1-hydroxyl-8-azaspirane[4,5]decane-8-carboxylic acid with easy-to-get raw materials, convenient operation, easy-to-control reaction and high yield Method for the synthesis of es...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/20
CPCC07D221/20
Inventor 于凌波史桂滨李甜甜孙宝龙金星崔梦佳刘冬吕秀芝吴明昆庞洲宋艾芳徐博任文武马汝建尚慕宏
Owner WUXI APPTEC (TIANJIN) CO LTD
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