Synthesis method of 1-oxo-2,6-diazaspiro[3.5]nonane-6-tert-butyl formate

A technology for the synthesis of tert-butyl formate, which is applied in the production of bulk chemicals and organic chemistry, can solve the problems of long synthetic routes and low overall yields, achieve short synthetic routes, save raw material costs, and design reasonable reaction processes Effect

Inactive Publication Date: 2021-08-06
SHANGHAI SYNTHEALL PHARM CO LTD
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Problems solved by technology

Although there are a few reports in the literature on the synthesis method of tert-butyl 1-oxyidene-2,6-diazaspiro[3.5]nonane-6-carboxylate, the synthetic route is long and the overall yield is not high.

Method used

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  • Synthesis method of 1-oxo-2,6-diazaspiro[3.5]nonane-6-tert-butyl formate
  • Synthesis method of 1-oxo-2,6-diazaspiro[3.5]nonane-6-tert-butyl formate
  • Synthesis method of 1-oxo-2,6-diazaspiro[3.5]nonane-6-tert-butyl formate

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Embodiment 1

[0033] The reaction formula of the present embodiment is as follows:

[0034]

[0035] Step 1: In N 2 Under protection, diisopropylamine (7.1mL, 50.66mmol) and anhydrous tetrahydrofuran (190mL) were added, cooled to -70°C, 2.5M n-butyllithium (20mL, 52mmol) was added dropwise, and stirred for 0.5 hours to prepare diisopropylamine Lithium propylamide. Then, a solution of compound 2 (12g, 46.63mmol) in tetrahydrofuran (50mL) was added, kept at -70°C, and stirring was continued for 1 hour, a solution of compound 1 (3.5g, 23.94mmol) in tetrahydrofuran (50mL) was added, kept at -70°C °C, stirring was continued for 1 hour. Return to room temperature and continue stirring for 16 hours. A solution of ammonium chloride (18 g) in water (120 mL) was added to quench the reaction and the organic phase was separated and washed with water (200 mL). The organic phase was separated, concentrated and purified by column chromatography (petroleum ether / ethyl acetate=6 / 1-2 / 1) to obtain comp...

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Abstract

The invention discloses a synthesis method of 1-oxo-2,6-diazaspiro[3.5]nonane-6-tert-butyl formate. The synthesis method comprises the following steps: in a first reaction solvent and an inert atmosphere, reacting a compound 2 with a compound 1 under the action of alkali to obtain a compound 3; and 2, removing a benzyl protecting group from the compound 3 to obtain a compound 4. The disclosed method has the advantages of easily available raw materials, convenience in operation, short route, high total yield, suitability for industrial production and the like, and mainly solves the technical problem that no suitable industrial synthesis method exists at present.

Description

technical field [0001] The invention relates to the field of chemical synthesis methods, in particular to a method for synthesizing tert-butyl 1-oxyethylene-2,6-diazaspiro[3.5]nonane-6-carboxylate. Background technique [0002] Compound 1-oxyylidene-2,6-diazaspiro[3.5]nonane-6-carboxylic acid tert-butyl ester (CAS: 1250997-43-3) and related derivatives are widely used in medicinal chemistry and organic synthesis application. Although there are a few literature reports on the synthesis method of tert-butyl 1-oxyylidene-2,6-diazaspiro[3.5]nonane-6-carboxylate, the synthetic route is long and the overall yield is not high. [0003] Therefore, it is necessary to develop a synthetic method that is easy to obtain raw materials, easy to operate, easy to control the reaction, short in route, high in overall yield, and suitable for industrial production. Contents of the invention [0004] The technical problem to be solved by the present invention is to provide a method for synth...

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 周强张大为孙春于凌波徐学芹毛延军董径超马汝建徐艳白有银焦家盛兰倩倩高明飞姚宝元赵廷谭汝鹏王曦贾涛赵艳美巴苏伟刘双燕魏昕睿
Owner SHANGHAI SYNTHEALL PHARM CO LTD
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