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Synthesis method of tert-butyl-1, 7-diazaspiro [3.5] nonane-1-formate

A technology of diazaspiro and synthesis method, which is applied in the field of synthesis of tert-butyl-1,7-diazaspiro[3.5]nonane-1-carboxylate, and can solve the problems such as no suitable industrial synthesis method , to achieve the effect of reasonable reaction process design, short route and appropriate yield

Active Publication Date: 2020-09-04
SHANGHAI STA PHARMA R&D CO LTD +1
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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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  • Synthesis method of tert-butyl-1, 7-diazaspiro [3.5] nonane-1-formate
  • Synthesis method of tert-butyl-1, 7-diazaspiro [3.5] nonane-1-formate

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Embodiment

[0012] Step 1: Dissolve compound 1 (200g, 2.38mol) in ethanol (1.3 L) at 25°C, add ammonium acetate (138 g, 1.80mol), heat up to 80°C for 1 hour; add ethylmalonic acid dropwise Ester (186 g, 1.41 mol) was reacted under reflux for 4 hours. TLC (petroleum ether / ethyl acetate volume ratio = 5 / 1) showed that the reaction of compound 1 was complete. The reaction solution was concentrated under reduced pressure, and the obtained crude product was neutralized to pH = 8 by adding 1N sodium hydroxide solution, and then extracted with ethyl acetate (0.5 L x 3). The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by chromatography to obtain compound 2 (169.2 g, yield: 41%).

[0013] Step 2: Dissolve compound 2 (132 g, 0.415 mol) in tetrahydrofuran (1 L), cool to 0°C, and add lithium borohydride (13.7 g, 0.623 mol) in batches. The reaction system was stirred for 0.5 hour...

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Abstract

The invention relates to a synthesis method of tert-butyl-1, 7-diazaspiro [3.5] nonane-1-formate, and mainly solves the technical problem that no suitable industrial synthesis method exists at present. The method comprises the following seven steps: 1, reacting a compound 1 with ethyl malonate added into a solvent ethanol to obtain a compound 2; 2, reacting the compound 2 with lithium borohydridein tetrahydrofuran to obtain a compound 3; 3, reacting the compound 3 with p-toluenesulfonyl chloride in dichloromethane to obtain a compound 4; 4, adding cesium carbonate into the compound 4 in acetonitrile serving as a solvent for cyclization to obtain a compound 5; 5, adding magnesium chips into the compound 5 in methanol serving as a solvent for reduction to obtain a compound 6, 6, reacting the compound 6 with Boc anhydride in dichloromethane to obtain a compound 7, and 7, reacting the compound 7 with palladium on carbon in methanol to obtain a final compound 8.

Description

technical field [0001] The invention relates to a synthesis method of tert-butyl-1,7-diazaspiro[3.5]nonane-1-carboxylate. Background technique [0002] The compound tert-butyl-1,7-diazaspiro[3.5]nonane-1-carboxylate (CAS: 1216936-29-6) and related derivatives are widely used in medicinal chemistry and organic synthesis. Currently, there are few reports on the synthesis of tert-butyl-1,7-diazaspiro[3.5]nonane-1-carboxylate. Therefore, it is necessary to develop a synthetic method that is easy to obtain raw materials, easy to operate, easy to control the reaction, suitable for overall yield, and suitable for industrial production. Contents of the invention [0003] The purpose of this invention is to develop a kind of raw material that is easy to get, easy to operate, easy to control the reaction, and the synthesis of tert-butyl-1,7-diazaspiro[3.5]nonane-1-carboxylate with higher yield method. It mainly solves the technical problem that there is no suitable industrial syn...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/10
CPCC07D471/10Y02P20/55
Inventor 张大为周强高明飞姚宝元兰倩倩赵廷王曦卫维魏昕睿谭汝鹏贾涛白有银孙春付新雨于凌波马汝建
Owner SHANGHAI STA PHARMA R&D CO LTD
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