Tert-butylhexahydro-2H-pyrrole[1,4]oxazepine-7(3H)-carboxylic ester preparation method

A technology of oxazepane and carboxylate, which is applied in the field of preparation of tert-butylhexahydro-2H-pyrrole[1,4]oxazepane-7(3H)-carboxylate, It can solve the problems of no suitable industrial synthesis method, etc., and achieve the effects of short synthesis route, easy reaction and convenient operation.

Inactive Publication Date: 2020-02-28
WUXI APPTEC
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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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  • Tert-butylhexahydro-2H-pyrrole[1,4]oxazepine-7(3H)-carboxylic ester preparation method

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Embodiment 1

[0010] Example 1: a, compound 1 (500 g, 2.95 mol) and N-benzyl hydroxylamine (659 g, 4.1 mol), potassium acetate (434 g, 4.43 mol), paraformaldehyde (500 g, 5.0 mol) Dissolve in ethanol (5 L), heat the mixture to reflux, react for 24 hours, TLC (petroleum ether / ethyl acetate volume ratio=10 / 1) shows that the reaction is complete. The reaction system was cooled to room temperature, 3L of water was added, and the reaction solution was adjusted to pH=11 with solid sodium carbonate, then extracted with ethyl acetate, the organic phase was dried with anhydrous sodium sulfate, and distilled under reduced pressure to obtain the crude compound 2 in brown oil (1 kg).

[0011] b. Dissolve compound 2 (180 g, 0.56 mol) in methanol (2 L), then add Raney nickel (100 g, 3.7 mol) into the system, control the reaction temperature at room temperature, and react at a pressure of 15 psi for 2 hours. TLC (petroleum ether / ethyl acetate volume ratio=1 / 1) showed that the reaction was complete. The ...

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Abstract

The invention relates to a tert-butylhexahydro-2H-pyrrole[1,4]oxazepine-7(3H)-carboxylic ester preparation method. A purpose of the invention is mainly to solve the technical problem of no industrialsynthesis method in the prior art. According to the invention, the method comprises the following six steps: generating a compound 2 from a compound 1 and N-benzyl hydroxylamine under the action of potassium acetate, 2, carrying out ring opening under the action of raney nickel to obtain a compound 3, carrying out a reaction on the compound 3 and chloroacetyl chloride to obtain a compound 4, obtaining a cyclization product compound 5 under the action of potassium tert-butoxide, carrying out borane reduction to obtain a compound 6, and finally obtaining a target product compound 7 under the action of palladium carbon. According to the invention, the compound obtained by the method is a useful intermediate or product for synthesizing a lot of medicines.

Description

technical field [0001] The present invention relates to a preparation method of tert-butylhexahydro-2H-pyrrole[1,4]oxazepane-7(3H)-carboxylate, namely a kind of (5aS,8aS)-tert-butyl Preparation method of hexahydro-2H-pyrrole[3,4-f][1,4]oxazepane-7(3H)-carboxylate (CAS: 1251006-15-1). Background technique [0002] (5aS,8aS)-tert-butylhexahydro-2H-pyrrole[3,4-f][1,4]oxazepane-7(3H)-carboxylate and related derivatives in medicinal chemistry It has wide applications in organic synthesis. There are few reports on the synthesis of (5aS,8aS)-tert-butylhexahydro-2H-pyrrole[3,4-f][1,4]oxazepane-7(3H)-carboxylate. There is a certain risk in similar literature reactions, and the route is long and the yield is low. 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 (5aS,8a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/04
CPCC07D498/04
Inventor 史桂滨吕秀芝孙宝龙赵强楚晓丹刘冬甄蕊崔梦佳于凌波
Owner WUXI APPTEC
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