Synthesis method of 8-oxo-5-oxa-2-diazaspiro [3.5] nonane-2-tert-butyl formate

A technology of tert-butyl formate and a synthesis method, which is applied in directions such as organic chemistry, can solve problems such as no suitable industrial synthesis method, and achieves the effects of reasonable reaction process design, convenient operation and easy reaction.

Inactive Publication Date: 2017-11-24
SHANGHAI STA PHARMA R&D CO LTD
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Mainly solve the technical problem that there is

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  • Synthesis method of 8-oxo-5-oxa-2-diazaspiro [3.5] nonane-2-tert-butyl formate
  • Synthesis method of 8-oxo-5-oxa-2-diazaspiro [3.5] nonane-2-tert-butyl formate

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[0012] The first step: Dissolve n-butyl lithium (6.97 mL, 17.43 mol) in tetrahydrofuran (9 L), then add compound 2 (500 g, 5.81 mol) and TMEDA (202.5 g, 1.74 mol), the reaction was stirred for one hour. Then compound 1 (1.07 Kg, 6.27 mol) previously dissolved in tetrahydrofuran (2 L) was added dropwise into the above reaction system at 0°C to 10°C, and the reaction was maintained at 0°C to 10°C for 2 hours. TLC (petroleum ether / ethyl acetate volume ratio = 3 / 1) showed that the reaction was complete. Saturated ammonium chloride aqueous solution (1.5 L) was added to the reaction system, then extracted with ethyl acetate (1.5 L x 3), the organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product, which was purified by silica gel column (Gradient elution: petroleum ether / ethyl acetate ~ petroleum ether / ethyl acetate volume ratio = 5:1 ~ 0:1) Yellow oily compound 3 (1.13 Kg crude product) was obtained with a yield of 2...

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Abstract

The invention relates to a synthesis method of 8-oxo-5-oxa-2-diazaspiro [3.5] nonane-2-tert-butyl formate, and mainly solves the technical problem that no industrial method suitable for industrial synthesis exists in the prior art. The synthesis method comprises three steps that 1, a compound 1, a compound 2 and TMEDA react in a solvent of tetrahydrofuran to obtain a compound 3; 2, the compound 3 is subjected to intramolecularly ring closing to obtain a compound 4 under the gathering effects of chlorine tosylate by using n-butyllithium as the alkali; 3, the compound 4 and ozone react to obtain a final compound 5. A reaction formula is shown in the specification.

Description

technical field [0001] The invention relates to a synthesis method of compound 8-oxoylidene-5-oxa-2-azaspiro[3.5]nonane-2-carboxylic acid tert-butyl ester. Background technique [0002] The compound tert-butyl 8-oxylidene-5-oxa-2-azaspiro[3.5]nonane-2-carboxylate (PubChem CompoundID: 124253235) and related derivatives are widely used in medicinal chemistry and organic synthesis . Currently, there are few reports on the synthesis of tert-butyl 8-oxylidene-5-oxa-2-azaspiro[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 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 8-oxygenide-5-oxa-2-azaspiro[3.5]nonane-2-carboxylic acid with higher yield Synthesis method of te...

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Application Information

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IPC IPC(8): C07D491/107
CPCC07D491/107
Inventor 张大为周强赵红双高明飞于智宇姚宝元卢荣昌白有银孙春刘雨雷韩华欣付新雨卢仔倚李旭东于凌波马汝建
Owner SHANGHAI STA PHARMA R&D CO LTD
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