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Method for preparing 4-aminobutyrate derivatives

An aminobutyrate and derivative technology, which is applied in chemical instruments and methods, cyanide reaction preparation, organic compound preparation, etc., can solve the tedious steps, environmental pollution and low yield of 4-aminobutyrate derivatives and other problems, to achieve the effect of solving the complex synthesis steps, simple operation and low cost

Active Publication Date: 2018-04-10
HARBIN INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a method for preparing 4-aminobutyrate derivatives in order to solve the problems of cumbersome steps, low yield and environmental pollution in the existing method for synthesizing 4-aminobutyrate derivatives

Method used

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  • Method for preparing 4-aminobutyrate derivatives
  • Method for preparing 4-aminobutyrate derivatives
  • Method for preparing 4-aminobutyrate derivatives

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specific Embodiment approach 1

[0013] Specific embodiment one: a method for preparing 4-aminobutyrate derivatives in this embodiment comprises the following steps:

[0014] Dissolve diarylamine derivatives, olefin derivatives and ethyl diazoacetate in an organic solvent in a nitrogen atmosphere at room temperature, then add a photocatalyst and mix well, then place it under a blue LED light for light reaction, spin After steaming to remove the solvent, through silica gel column chromatography separation and purification, the resulting product is 4-aminobutyrate derivatives; the mol ratio of diarylamine derivatives, olefin derivatives, ethyl diazoacetate and photocatalyst is 1:( 2-4):(4-8):(0.1-0.5).

[0015] Wherein the chemical structural formula of diarylamine derivative is:

[0016] The chemical structural formula of olefin derivatives is:

[0017] The chemical structural formula of ethyl diazoacetate is:

[0018] Among them, R 1 , R 2 is alkyl, alkoxy or halogen, R 3 Is aryl, ester or alkyl.

...

specific Embodiment approach 2

[0020] Specific embodiment two: the difference between this embodiment and specific embodiment one is: olefin derivatives are styrene, β-methylstyrene, 4-methylstyrene, 4-chlorostyrene, 3-chlorostyrene or ethyl acrylate. Others are the same as the first embodiment.

specific Embodiment approach 3

[0021] Embodiment 3: The difference between this embodiment and Embodiment 1 or 2 is that the organic solvent is acetonitrile, tetrahydrofuran, methanol, dimethyl sulfoxide or N,N-dimethylformamide. Others are the same as those in Embodiment 1 or 2.

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Abstract

The invention discloses a method for preparing 4-aminobutyrate derivatives, and relates to a method for preparing the 4-aminobutyrate derivatives. The purpose of the invention is to solve the problemsof complicated steps, a low yield, and environmental pollution in the synthesis of the 4-aminobutyrate derivatives by using conventional methods. The method comprises the following steps: a diarylamine derivative, an olefin derivative and ethyl diazoacetate are dissolved into an organic solvent under a nitrogen atmosphere and room temperature, then a photocatalyst is added, mixing is performed uniformly, the mixed material is placed below a blue LED lamp, an illumination reaction is performed, rotary evaporation is performed to remove the solvent, chromatography separation purification is performed by using a silica gel column, and therefore the product, one 4-aminobutyrate derivative, is obtained. The reaction in the method provided by the invention can be performed under a normal temperature and normal pressure, the reaction conditions are mild, the yield can reach 80%, and the method has the advantages of simple operation, no pollution, safety, environmental friendliness and low costs, and is applied to the field of organic synthesis.

Description

technical field [0001] The invention relates to a method for preparing 4-aminobutyrate derivatives. Background technique [0002] 4-aminobutyric acid, GABA for short, is a very important inhibitory neurotransmitter in the central nervous system, widely distributed in the nervous tissue of animals. According to literature reports, it has a variety of biological activities. As shown in the following formula, compounds 1-3 are typical biologically active natural products containing a 4-aminobutyrate skeleton. Among them, compound 1 is an inhibitor of cannabinoid receptor CB1, compound 2 is a drug for treating inflammation, and compound 3 is an inhibitor of deacetylase. [0003] [0004] GABA was artificially synthesized as early as 1883. However, most of the synthesis methods use Lewis acid or transition metal catalyst system, which will inevitably cause great burden and damage to the environment, and the steps are cumbersome and the yield is only about 40%. Therefore, i...

Claims

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Application Information

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IPC IPC(8): C07C227/10C07C229/34
Inventor 杨超马娜李冰
Owner HARBIN INST OF TECH
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