2-((1s3ar7ar)-5-tert-butoxycarbonyltetrahydrofuro[3,4]piperidine-1)acetic acid

A technology of tert-butoxycarbonyltetrahydrofuran and tetrahydrofuran, which is applied in the field of 2-((1S3aR7aR)-5-tert-butoxycarbonyltetrahydrofuro[3,4]piperidine-1)acetic acid preparation method, can solve the problem of unsuitable industrial synthesis Method and other issues, to achieve the effect of reasonable reaction process design, simple route, and strong repeatability
CN107383035BActive Publication Date: 2019-06-25SHANGHAI SYNTHEALL PHARM CO LTD +3
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
SHANGHAI SYNTHEALL PHARM CO LTD
Publication Date
2019-06-25

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Abstract

The invention relates to a preparation method of 2-((1S3aR7aR)-5-tert-butyloxycarbonyltetrahydrofuro[3,4]piperidine-1)acetic acid. The preparation method comprises 11 steps: carrying out esterification on a dicarboxylic acid piperidine compound 1 in thionyl chloride to obtain a diester compound 2; then reducing a pyridine ring by utilizing palladium carbon to obtain a compound 3; then taking the compound 3 to react with Boc acid anhydride to obtain a Boc protected compound 4; hydrolyzing the compound 4 by utilizing lithium hydroxide to obtain a dicarboxylic acid compound 5; carrying out ring closure in acetic anhydride to obtain a compound 6; carrying out reduction and ring opening by utilizing NaBH4 to obtain a mixture of position isomerism compounds 7A and 7B; carrying out the ring closure in the presence of iodomethane and potassium carbonate to generate position isomerism lactone 8A and 8B; step 8, reducing the 8A, obtained by column passing separation, by utilizing DIBAH (Diisobutylaluminum Hydride) to obtain a compound 9; carrying out Wittig reaction to obtain a compound 10; carrying out Michael addition under an alkaline condition to obtain a compound 11; finally, hydrolyzing the compound 11 under the alkaline condition to obtain a final compound.
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Description

technical field

[0001] The invention relates to a method for synthesizing compound 2-((1S3aR7aR)-5-tert-butoxycarbonyltetrahydrofuro[3,4]piperidine-1)acetic acid. Background technique

[0002] Compound 2-((1S3aR7aR)-5-tert-butoxycarbonyltetrahydrofuro[3,4]piperidine-1)acetic acid (CAS: 646518-35-6 ) and related derivatives are widely used in medicinal chemistry and organic synthesis. application. At present, there is no literature report on the synthesis method of 2-((1S3aR7aR)-5-tert-butoxycarbonyltetrahydrofuro[3,4]piperidine-1)acetic acid. 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 2-((1S3aR7aR)-5-tert-butoxycarbonyltetrahydrofuro[3,4]piperidine-1) with raw materials that are easy to get, easy to operate, easy...

Claims

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