4-tert-butoxycarbonyl-hexahydro-2H-furo [3,2-b] pyrrole-6-carboxylic acid synthetic method

A technology of tert-butoxycarbonyl and synthesis method, which is applied in the field of synthesis of 4-tert-butoxycarbonyl-hexahydro-2H-furo[3,2-b]pyrrole-6-carboxylic acid, can solve the problem of unsuitable industrialization Synthetic methods and other issues, to achieve the effect of convenient operation, easy reaction, and short route

Inactive Publication Date: 2016-06-15
SHANGHAI SYNTHEALL PHARM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • 4-tert-butoxycarbonyl-hexahydro-2H-furo [3,2-b] pyrrole-6-carboxylic acid synthetic method
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  • 4-tert-butoxycarbonyl-hexahydro-2H-furo [3,2-b] pyrrole-6-carboxylic acid synthetic method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0010] Example 1: Compound 1 (8.0g, 0.0310mol) was dissolved in tetrahydrofuran (60mL), cooled to -20 degrees Celsius, and potassium tert-butoxide (8.7g, 0.0777mol) was added, stirred for half an hour, and then added dropwise under nitrogen protection After the addition of bromochloroethane (6.5 g, 0.0451 mol), the temperature of the reaction was raised to 15 degrees Celsius overnight. TLC (petroleum ether: ethyl acetate volume ratio=5 / 1, R f =0.5) showed that the reaction was complete, the reaction mixture was quenched with saturated ammonium chloride solution (30 mL), and extracted with ethyl acetate (20 mLx3). The organic phase was dried with anhydrous sodium sulfate and concentrated, the residue was purified by column chromatography, the eluent ratio was (petroleum ether: ethyl acetate volume ratio = 20 / 1), and compound 2 in yellow oil was obtained after removing the solvent (9.9 g), yield 100%.

[0011] Compound 2 (9.9 g, 0.0310 mol) was dissolved in tetrahydrofuran (80...

Embodiment 2

[0017] Example 2: Dissolve compound 1 (80g, 0.310mol) in tetrahydrofuran (600mL), cool to -20 degrees Celsius, add potassium tert-butoxide (87g, 0.777mol), stir for half an hour, then add bromochloride dropwise under nitrogen protection Ethane (65 g, 0.451 mol), after the addition was complete, the reaction was warmed to 15°C overnight. TLC (petroleum ether: ethyl acetate volume ratio=5 / 1, R f =0.5) showed that the reaction was complete, the reaction mixture was quenched with saturated ammonium chloride solution (300mL), and extracted with ethyl acetate (200mLx3). The organic phase was dried with anhydrous sodium sulfate and concentrated, the residue was purified by column chromatography, the eluent ratio was (petroleum ether: ethyl acetate volume ratio = 20 / 1), and compound 2 in yellow oil was obtained after removing the solvent (95g), yield 96%.

[0018] Compound 2 (95g, 0.298mol) was dissolved in tetrahydrofuran (800mL), sodium hydrogen (12.4g, 0.31mol) was added under ni...

Embodiment 3

[0024] Example 3: Dissolve compound 1 (300 g, 1.18 mol) in tetrahydrofuran (3.0 L), cool to -20 degrees Celsius, add potassium tert-butoxide (330 g, 2.95 mol), stir for half an hour, then add bromine dropwise under nitrogen protection Ethyl chloride (253g, 1.77mol), after the addition was complete, the reaction was warmed to 15°C overnight. TLC (petroleum ether: ethyl acetate volume ratio=5 / 1, R f =0.5) showed that the reaction was complete, the reaction mixture was quenched with saturated ammonium chloride solution (1.0L), and extracted with ethyl acetate (1.0Lx3). The organic phase was dried with anhydrous sodium sulfate and then concentrated, and the residue was purified by column chromatography, the eluent ratio was (petroleum ether: ethyl acetate volume ratio = 20 / 1), and compound 2 in yellow oil was obtained after removing the solvent (372g), yield 98.8%.

[0025] Compound 2 (372g, 1.18mol) was dissolved in tetrahydrofuran (3.0L), sodium hydrogen (70g, 1.77mol) was add...

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Abstract

The present invention relates to a 4-tert-butoxycarbonyl-hexahydro-2H-furo [3,2-b] pyrrole-6-carboxylic acid synthetic method and mainly solves a technical problem that currently no suitable industrial synthetic method exists. The synthetic method comprises the following four steps: firstly, a compound 1 is subjected to an alkylation reaction with bromo chloroethane to obtain a compound 2; then the compound 2 is subjected to an intra-molecular cyclization reaction to obtain a compound 3; the compound 3 is subjected to a double bond hydrogenation reduction to obtain a compound 4; and the compound 4 is hydrolyzed to obtain a compound 5. The response equations are described as follows.

Description

technical field [0001] A method for synthesizing the compound 4-tert-butoxycarbonyl-hexahydro-2H-furo[3,2-b]pyrrole-6-carboxylic acid (CAS: 1445951-57-4) involved in the present invention. Background technique [0002] The compound 4-tert-butoxycarbonyl-hexahydro-2H-furo[3,2-b]pyrrole-6-carboxylic acid and related derivatives are widely used in medicinal chemistry and organic synthesis. Currently, the synthesis of 4-tert-butoxycarbonyl-hexahydro-2H-furo[3,2-b]pyrrole-6-carboxylic acid is difficult. Therefore, it is necessary to develop a synthetic method with readily available raw materials, convenient operation, easy control of the reaction, and suitable overall yield. Contents of the invention [0003] The purpose of the present invention is to develop a kind of 4-tert-butoxycarbonyl-hexahydro-2H-furo[3,2-b]pyrrole-6- Synthesis of carboxylic acids. It mainly solves the technical problem that there is no suitable industrial synthesis method at present. [0004] Techni...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/048
Inventor 李文鹏任文武陈雅婷张金宝孟庆洪邱继平刘洋邢少廷于涵赵东王庆伟孙宝龙宁振翠靳爱杰卫凯龙要加军袁晓斌于凌波何振民马汝建陈民章傅小勇王文贵
Owner SHANGHAI SYNTHEALL PHARM CO LTD
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