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Synthesis method of cis5-tert-butyl-3A-methyl-tetrahydro 1H-furan[3,4 c] pyrrole 3A,5(3H) dicarboxylic ester

A synthetic method, the technology of tert-butyl, applied in the direction of organic chemistry, organic chemistry, etc., can solve the problem of no suitable industrial synthesis method, and achieve the effect of reasonable reaction process design, easy reaction and convenient operation

Inactive Publication Date: 2017-11-24
上海药明康德新药开发有限公司 +4
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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 cis5-tert-butyl-3A-methyl-tetrahydro 1H-furan[3,4 c] pyrrole 3A,5(3H) dicarboxylic ester
  • Synthesis method of cis5-tert-butyl-3A-methyl-tetrahydro 1H-furan[3,4 c] pyrrole 3A,5(3H) dicarboxylic ester

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Embodiment

[0012] Step 1: Dissolve compound 1 (330 g, 1.77 mol) in ethanol (2000 mL), then add sodium borohydride (67.3 g, 1.77 mol) at 0°C, then react at 0°C for 2 hours, TLC (petroleum ether / Ethyl acetate volume ratio = 5 / 1) shows the completion of the reaction. 200 mL H 2 O was poured into the reaction solution, and then the ethanol was swirled out. The aqueous phase was extracted 3 times with 600 mL ethyl acetate. Na for organic phase 2 SO 4 After drying, it was concentrated under reduced pressure to obtain the crude compound 2, which was directly used in the next step.

[0013] Step 2: Dissolve compound 2 (267 g, 1.43 mol) in anhydrous THF (1500 mL), then slowly add PPh in batches at 0 °C 3 (408 g, 1.56 mol) and DIAD (315 g, 1.56 mol). Then the reaction solution was reacted at 25° C. for 16 hours. Then the crude product obtained by concentrating the reaction solution under reduced pressure was purified by silica gel column chromatography (gradient elution: petroleum ether / et...

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Abstract

The invention relates to a synthesis method of cis5-tert-butyl-3A-methyl-tetrahydro 1H-furan[3,4 c] pyrrole 3A,5(3H) dicarboxylic ester. The method mainly solves the technical problem that no proper industrial synthesis method exists in the prior art. The method comprises five steps that: 1, a compound 1 uses sodium borohydride as a reducing agent to react in an ethanol solvent to obtain a compound 2; 2, the compound 2 uses tetrahydrofuran as a solvent to obtain a compound 3 under the effects of triphenylphosphine and diisopropyl azodicarboxylate; 3, the compound 3 and the N-methoxymethyl-N-(trimethylsilyl) benzylamine use dichloromethane as a solvent to obtain a compound 4 through room temperature reduction under the action of trifluoroacetic acid; 4, the compound 4 and thionyl chloride react under the methanol backflow condition to obtain a compound 5; 5, the compound 5 uses palladium hydroxide catalysts and Boc anhydride auxiliary agents to obtain a final compound 6 through catalytic hydrogenation reaction.

Description

technical field [0001] The invention relates to a synthesis method of the compound cis-5-tert-butyl-3A-methyl-tetrahydro-1H-furo[3,4-c]pyrrole-3A,5(3H)-dicarboxylate. Background technique [0002] The compound cis-5-tert-butyl-3A-methyl-tetrahydro-1H-furo[3,4-c]pyrrole-3A,5(3H)-dicarboxylate (MDL: MFCD27997334) and related Derivatives are widely used in medicinal chemistry and organic synthesis. Currently, there are few reports on the synthesis of cis-5-tert-butyl-3A-methyl-tetrahydro-1H-furo[3,4-c]pyrrole-3A,5(3H)-dicarboxylate. 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 cis-5-tert-butyl-3A-methyl-tetrahydro-1H-furo[3,4 which has easy-to-get raw materials, convenient operation and easy-to-control reaction and hi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/048C07D307/24C07D307/30
CPCC07D491/048C07B2200/07C07D307/24C07D307/30
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 上海药明康德新药开发有限公司
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