Preparation method of 3-oxymethylene-7-oxa-2,10-diazaspiro[4,6] undecane-10-tert-butyl formate

A kind of technology of tert-butyl formate and diazaspiro, which is applied to the preparation of 3-oxyidene-7-oxa-2,10-diazaspiro[4.6]undecane-10-carboxylate tert-butyl ester In the field of law, it can solve the problem of no industrial synthesis method, and achieve the effect of short route and reasonable design.

Inactive Publication Date: 2019-03-19
上海药明康德新药开发有限公司
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Mainly solve the technical problems that t...

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  • Preparation method of 3-oxymethylene-7-oxa-2,10-diazaspiro[4,6] undecane-10-tert-butyl formate

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[0013] Step 1: Dissolve 20 grams of sodium hydride in 500 milliliters of anhydrous tetrahydrofuran, add a tetrahydrofuran solution of triethyl phosphonoacetate dropwise at 0°C, and after 1 hour of reaction, add 170 grams of a tetrahydrofuran solution of raw material 1 dropwise (170 g compound dissolved in 2 liters of tetrahydrofuran), after the addition was complete, the reaction solution was raised to 20°C for 3 hours. After the reaction was completed, it was quenched with saturated ammonium chloride, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and rotary evaporated under reduced pressure to obtain 248 g of crude compound 2, which was directly used in the next step.

[0014] The second step: dissolve 248 grams of crude compound 2, 111.4 grams of nitromethane and 340.8 grams of tetrabutylammonium fluoride in 3 liters of tetrahydrofuran, and react at 70 ° C for 12 hours; after the reaction is completed, the reaction solution is cooled to room temperature a...

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Abstract

The invention relates to a synthetic method of 3-oxymethylene-7-oxa-2,10-diazaspiro[4,6] undecane-10-tert-butyl formate and primarily solves the technical problem that no proper industrial synthetic methods are available in the prior art. The method comprises the following three steps: S1, first dissolving a compound 1 in tetrahydrofuran and adding sodium hydride and triethyl phosphonoacetate to carry out a Wittig reaction to obtain a compound 2; S2, dissolving the compound 2, nitromethane and Tetrabutyl ammonium fluoride in tetrahydrofuran and heating the solution to react to generate a compound 3; and S3, dissolving the compound 3 ethanol and carrying out reduction and ring closing by raney nickel to obtain a compound 4; the reaction formula as shown in the description.

Description

technical field [0001] The invention relates to a method for synthesizing compound 3-oxygenide-7-oxa-2,10-diazaspiro[4.6]undecane-10-carboxylic acid tert-butyl ester. Background technique [0002] The compound tert-butyl 3-oxyylidene-7-oxa-2,10-diazaspiro[4.6]undecane-10-carboxylate (CAS: 1823269-80-2) and related derivatives in Medicinal Chemistry It has wide applications in organic synthesis. Currently, there are few reports on the synthesis of tert-butyl 3-oxylidene-7-oxa-2,10-diazaspiro[4.6]undecane-10-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 the present invention is to develop a kind of 3-oxosubunit-7-oxa-2,10-diazaspiro[4.6]undecane with easy to get raw material, easy operation, easy to control reaction and high yield -The preparation m...

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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 上海药明康德新药开发有限公司
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