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Synthesis method of trans-4-amino cyclohexanecarboxylic acid derivative

A technology of ethyl carbonylcyclohexyl carboxylate and a synthesis method, which is applied in the field of synthesis of pharmaceutical intermediate products, can solve problems such as inability to reduce costs and risks, and achieve the effects of simple routes, low cost, and easy-to-obtain raw materials

Inactive Publication Date: 2014-01-15
BAIYIN LANGYOU BIOLOGICAL PHARMA TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Since the above documents all need to use expensive noble metal catalysts to catalyze aromatic rings to cyclohexane rings, the cost cannot be reduced, and high-pressure reactions are required, which has certain risks.

Method used

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  • Synthesis method of trans-4-amino cyclohexanecarboxylic acid derivative
  • Synthesis method of trans-4-amino cyclohexanecarboxylic acid derivative
  • Synthesis method of trans-4-amino cyclohexanecarboxylic acid derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Example 1 The synthetic method of trans-4-aminocyclohexylcarboxylic acid derivative comprises the following steps:

[0023] (1) Dissolve ethyl 4-carbonylcyclohexyl carboxylate (SM) in tetrahydrofuran (THF) at a mass-to-liquid ratio of 1:35 (g / L), cool down to -80°C, and add 1mol / L tri-sec-butyl dropwise Lithium borohydride L-selectride tetrahydrofuran (THF) solution, keep the temperature at -80~-70°C, add it in 2 hours, keep it warm for half an hour; then add dropwise an aqueous solution of NaOH with a mass concentration of 8%, and keep the temperature at -80~ -70°C, finish adding in half an hour, dropwise add hydrogen peroxide with a mass concentration of 30%, keep the temperature at -80~-70°C, and finish adding in 2 hours; secondly, naturally raise the temperature to 0°C, add ethyl acetate for extraction, extraction times 2 Once, the organic layers were combined, and the organic layer was washed with a 10% aqueous solution of sodium sulfite in a mass concentratio...

Embodiment 2

[0030] Example 2 The synthetic method of trans-4-aminocyclohexylcarboxylic acid derivative comprises the following steps:

[0031](1) Dissolve ethyl 4-carbonylcyclohexyl carboxylate (SM) in tetrahydrofuran (THF) at a mass-to-liquid ratio of 1:15 (g / L), cool down to -80°C, and add 1mol / L tri-sec-butyl dropwise Lithium borohydride L-selectride tetrahydrofuran (THF) solution, keep the temperature at -80~-70°C, add it in 2 hours, keep it warm for half an hour; then add dropwise an aqueous solution of NaOH with a mass concentration of 8%, and keep the temperature at -80~ -70°C, finish adding in half an hour, dropwise add hydrogen peroxide with a mass concentration of 30%, keep the temperature at -80~-70°C, and finish adding in 2 hours; secondly, naturally raise the temperature to 0°C, add ethyl acetate for extraction, extraction times 2 Once, the organic layers were combined, and the organic layer was washed with a 10% aqueous solution of sodium sulfite in a mass concentratio...

Embodiment 3

[0038] Example 3 The synthetic method of trans-4-aminocyclohexylcarboxylic acid derivative comprises the following steps:

[0039] (1) Dissolve ethyl 4-carbonylcyclohexyl carboxylate (SM) in tetrahydrofuran (THF) at a mass-to-liquid ratio of 1:45 (g / L), cool down to -80°C, and add 1mol / L tri-sec-butyl dropwise Lithium borohydride L-selectride tetrahydrofuran (THF) solution, keep the temperature at -80~-70°C, add it in 2 hours, keep it warm for half an hour; then add dropwise an aqueous solution of NaOH with a mass concentration of 8%, and keep the temperature at -80~ -70°C, finish adding in half an hour, dropwise add hydrogen peroxide with a mass concentration of 30%, keep the temperature at -80~-70°C, and finish adding in 2 hours; secondly, naturally raise the temperature to 0°C, add ethyl acetate for extraction, extraction times 2 Once, the organic layers were combined, and the organic layer was washed with a 10% aqueous solution of sodium sulfite in a mass concentrati...

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Abstract

The invention relates to a synthesis method of a trans-4-amino cyclohexanecarboxylic acid derivative. The method comprises the following steps of: (1) dissolving 4-carbonyl cyclohexyl ethyl formate in tetrahydrofuran, dropwise adding tetrahydrofuran solution of lithium tri-sec-butylborohydride, aqueous solution of NaOH and hydrogen peroxide in sequence, performing ethyl acetate extraction, washing an organic layer, then separating liquid and concentrating the organic layer to obtain P1; (2) dissolving the P1 in methylene dichloride, adding triethylamine, methanesulfonyl chloride, water and hydrochloric acid aqueous solution in sequence, uniformly stirring and then separating organic phase, and washing, drying and concentrating the organic phase in sequence to obtain P2; (3) dissolving the P2 in dimethyl formamide, adding sodium azide and water in sequence, performing ethyl acetate extraction, and washing, drying and concentrating the organic layer in sequence to obtain P3; and (4) dissolving the P3 in ethanol, adding palladium carbon, hydrogenating at room temperature, keeping overnight, finally filtering off palladium carbon Pd / C, and performing decompression and concentration to obtain oily trans-4-amino cyclohexyl ethyl formate. The synthesis method has the advantages of concise line, low cost, readily available raw material and high safety.

Description

technical field [0001] The invention relates to a synthesis method of a pharmaceutical intermediate product, in particular to a synthesis method of trans-4-aminocyclohexylcarboxylic acid derivatives. Background technique [0002] The production of pharmaceutical intermediates integrates many disciplines such as organic chemical industry, fine chemical industry, biology, materials, computer, machinery, optics, and precision testing. It is a comprehensive multidisciplinary system engineering. Therefore, the production and development of pharmaceutical intermediate products not only reflects the development level of a country's fine chemical industry, but also reflects the development level of a country's chemical and pharmaceutical industry to a certain extent. Therefore, accelerating the production of pharmaceutical intermediate products is important for promoting The development of a country's chemical and pharmaceutical industries plays an important role. [0003] 4-Aminoc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C227/04C07C229/48
Inventor 陈雪松祁自和李尊恒
Owner BAIYIN LANGYOU BIOLOGICAL PHARMA TECH