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Preparation method of 2-((1S3aR7aR)-5-tert-butyloxycarbonyltetrahydrofuro[3,4]piperidine-1)acetic acid

A technology of tert-butoxycarbonyltetrahydrofuran and diisobutylaluminum hydride, which is applied in the field of 2-((1S3aR7aR)-5-tert-butoxycarbonyltetrahydrofuro[3,4]piperidine-1)acetic acid production method, capable of Solve the problems of no suitable industrial synthesis method, etc., and achieve the effect of reasonable reaction process design, strong repeatability and simple route

Active Publication Date: 2017-11-24
SHANGHAI SYNTHEALL PHARM CO LTD +3
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  • Description
  • Claims
  • Application Information

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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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  • Preparation method of 2-((1S3aR7aR)-5-tert-butyloxycarbonyltetrahydrofuro[3,4]piperidine-1)acetic acid
  • Preparation method of 2-((1S3aR7aR)-5-tert-butyloxycarbonyltetrahydrofuro[3,4]piperidine-1)acetic acid
  • Preparation method of 2-((1S3aR7aR)-5-tert-butyloxycarbonyltetrahydrofuro[3,4]piperidine-1)acetic acid

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Embodiment 1

[0013] At zero degrees, SOCl 2 (400 mL) was slowly added dropwise into methanol (2.0 L). After the dropwise addition, the solution was stirred at room temperature for 15 minutes. Compound 1 (200 g, 1.2 mol) was added to the above solution in batches, and then 2, 2-Dimethoxypropane (400 mL). After the dropwise addition, the reaction solution was refluxed overnight. TLC (dichloromethane / methanol volume ratio 10:1) showed the reaction was complete. The reaction solution was concentrated under reduced pressure, ethyl acetate (2.0 L) was added to the residue, and the pH value was adjusted to 8 with dimethylamine. The mixture was washed with water three times, each time with 1.0 L of water, the separated organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo, and the finally obtained residue was purified by silica gel column chromatography (gradient elution: petroleum ether / ethyl acetate volume ratio From 10 / 1 to 5 / 1 to 2 / 1) to obtain pure compound 2 as ...

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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.

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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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/048C07D213/80C07D213/803C07D211/62C07D211/60
CPCC07B2200/07C07D211/60C07D211/62C07D213/80C07D213/803C07D491/048
Inventor 陈远丽韩冰洋杨云龙王冰杜天源石美奂陆绘联于凌波马汝建
Owner SHANGHAI SYNTHEALL PHARM CO LTD
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