Synthesis method of 3-(1-aminocyclopropyl) methyl benzoate

A technology of methyl cyanobenzoate and methyl benzoate, which is applied in the field of synthesis of methyl 3-(1-aminocyclopropyl)benzoate, and achieves the effects of reasonable design, easy control and high yield

Inactive Publication Date: 2021-04-27
阿里生物新材料(常州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few literature reports on the synthesis method of methyl 3-(1-aminocyclopropyl)benzoate

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] A kind of synthetic method of 3-(1-aminocyclopropyl) methyl benzoate, the synthetic method is: 20g 3-cyanobenzoic acid methyl ester, 300mL toluene are put into reactor, stir, nitrogen protection, be cooled to -20°C, add 35g tetraisopropyl titanate, stir, then add 30g ethylmagnesium bromide, control the temperature -20°C, stir, finally add 40mL0.3mol / L boron trifluoride ether solution, keep warm, TLC Detection, the raw material reacts, add 3M hydrochloric acid (150mL) dropwise to the reaction solution, separate the liquid, keep the organic phase, extract the aqueous phase with 2-methyltetrahydrofuran 3 times (250mL*3), combine the organic phase, and saturated hydrogen carbonate Wash with sodium (200mL), separate the layers, and concentrate the organic phase to dryness. The sample was mixed with silica gel and passed through the column to obtain 20.9 g of a yellow oily substance, that is, methyl 3-(1-aminocyclopropyl)benzoate, with a yield of 95% and a purity of 99.2%.

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Embodiment 2

[0021] A kind of synthetic method of 3-(1-aminocyclopropyl) methyl benzoate, the synthetic method is: 20g 3-cyanobenzoic acid methyl ester, 300mL toluene are put into reactor, stir, nitrogen protection, be cooled to -30°C, add 35g tetraisopropyl titanate, stir, then add 30g ethylmagnesium bromide, control the temperature -30°C, stir, finally add 40mL0.3mol / L boron trifluoride ether solution, keep warm, TLC Detection, the raw material reacts, add 3M hydrochloric acid (150mL) dropwise to the reaction solution, separate the liquid, keep the organic phase, extract the aqueous phase with 2-methyltetrahydrofuran 3 times (250mL*3), combine the organic phase, and saturated hydrogen carbonate Wash with sodium (200mL), separate the layers, and concentrate the organic phase to dryness. The sample was mixed with silica gel and passed through the column to obtain 21.3 g of yellow oily substance, that is, methyl 3-(1-aminocyclopropyl)benzoate, with a yield of 96.9% and a purity of 99.1%.

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PUM

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Abstract

The invention belongs to the technical field of medical intermediates, and particularly relates to a synthetic method of 3-(1-aminocyclopropyl) methyl benzoate. The synthesis method comprises the following steps: taking methyl 3-cyanobenzoate as a raw material, reacting tetraisopropyl titanate with methyl 3-cyanobenzoate to form a complex, protecting ester groups in methyl 3-cyanobenzoate, performing addition reaction with ethyl magnesium bromide, and finally performing cyclization and reaction under the action of an acid environment provided by boron trifluoride, and obtaining 3-(1-aminocyclopropyl) methyl benzoate.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical intermediates, in particular to a method for synthesizing methyl 3-(1-aminocyclopropyl)benzoate. Background technique [0002] The synthetic method of the compound 3-(1-aminocyclopropyl)methyl benzoate and related derivatives are widely used in medicinal chemistry and organic synthesis. At present, there are few reports on the synthesis methods of methyl 3-(1-aminocyclopropyl)benzoate. 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] Technical problem to be solved by the present invention: aim at the problem of , provide a kind of synthetic method of 3-(1-aminocyclopropyl) methyl benzoate. [0004] In order to solve the problems of the technologies described above, the present invention adopts ...

Claims

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Application Information

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IPC IPC(8): C07C227/04C07C229/46
CPCC07C227/04C07C249/02C07C253/30C07C2601/02
Inventor 刘超戴红升
Owner 阿里生物新材料(常州)有限公司
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