Method for synthesizing tert-butyl 6-oxo-8-oxa-2, 5-diazaspiro[3.5]nonane-2-carboxylate

A technology of tert-butyl formate and diazaspiro, applied in the field of synthesis of 6-oxylidene-8-oxa-2,5-diazaspiro[3.5]nonane-2-carboxylate tert-butyl , can solve the problems of no suitable industrial synthesis methods, etc., and achieve the effects of reasonable reaction process design, easy reaction and convenient operation

Inactive Publication Date: 2019-03-22
SHANGHAI SYNTHEALL PHARM CO LTD
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Mainly solve the technical problem that there is

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  • Method for synthesizing tert-butyl 6-oxo-8-oxa-2, 5-diazaspiro[3.5]nonane-2-carboxylate
  • Method for synthesizing tert-butyl 6-oxo-8-oxa-2, 5-diazaspiro[3.5]nonane-2-carboxylate

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[0012] Step 1: Dissolve compound 1 (45 g, 0.22 mol) in N,N-dimethylformamide (500 mL), add paraformaldehyde (60.2 g, 0.66 mol), and cool down to 0°C , tetrabutylammonium fluoride (5.8 g, 0.02 mol) was added to the reaction solution. The reaction was kept at 0°C for 30 minutes, then warmed to room temperature and reacted for 15 hours and 30 minutes. TLC showed the reaction was complete. The reaction was filtered with diatomaceous earth, the filtrate was poured into water and extracted with ethyl acetate, and the organic phase was dried with anhydrous sodium sulfate to obtain a white solid compound 2 (47 g, 90% purity). Yield: 90%.

[0013] 1 (400 M; CDCl 3 )

[0014] δ4.43-4.40 (d, J = 10 Hz, 2 H), 4.20-4.18 (d, J = 9.2 Hz, 2 H), 4.15-4.12(d, J = 10 Hz, 2 H), ,1.46 (s, 9 H).

[0015] The second step: Compound 2 (200 g, 0.86 mol) was dissolved in acetone (1.5L), and cesium carbonate (561 g, 1.72 mol) and ethyl bromoacetate (172 g, 1.03 mol) were added successively at r...

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Abstract

The invention relates to a method for synthesizing tert-butyl 6-oxo-8-oxa-2, 5-diazaspiro[3.5]nonane-2-carboxylate, and mainly solves a technical problem of absence of a method suitable for industrialsynthesis at present. The method provided by the invention comprises the following three steps: step one, firstly enabling a compound 1, paraformaldehyde and tetrabutylammonium fluoride added into asolvent N, N-dimethylformamide to be in reaction to obtain a compound 2; step two, enabling the compound 2, ethyl bromoacetate and cesium carbonate to be in reaction in acetone to obtain a compound 3;and step three, enabling the compound 3 and iron and ammonium chloride to be in reaction in ethanol and water to obtain a final compound 4, wherein a reaction formula is as shown in the Specification.

Description

technical field [0001] The invention relates to a synthesis method of compound 6-oxoylidene-8-oxa-2,5-diazaspiro[3.5]nonane-2-carboxylic acid tert-butyl ester. Background technique [0002] The compound 6-oxyylidene-8-oxa-2,5-diazaspiro[3.5]nonane-2-carboxylate tert-butyl ester (CAS: 1251000-12-0) and related derivatives are used in medicinal chemistry and Widely used in organic synthesis. Currently, there are few reports on the synthesis of tert-butyl 6-oxylidene-8-oxa-2,5-diazaspiro[3.5]nonane-2-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 object of the invention is to develop a kind of 6-oxosubunit-8-oxa-2,5-diazaspiro[3.5]nonane- Synthetic method of 2-tert-butyl formate. It mainly solves the technical problem that there is no suitable industrial synthe...

Claims

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Application Information

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IPC IPC(8): C07D498/10
CPCC07D498/10
Inventor 张大为周强白有银高明飞付新雨姚宝元谭汝鹏孔祥南刘鲜赵廷王曦孙春卢荣昌刘雨雷魏昕睿于凌波马汝建
Owner SHANGHAI SYNTHEALL PHARM CO LTD
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