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Reductive amination and resolution of isochroman-4-one

A technology of isochroman and amination, applied in the field of synthesis and resolution of chiral amines, to achieve the effect of simple operation, high purity and good product yield

Inactive Publication Date: 2017-02-15
王际菊
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the existing related research, the method of how to prepare isochroman-4-amine is mainly to first use sodium borohydride to make isochroman-4-alcohol, then in toluene solvent with diphenylphosphoric azide and DBU reaction (Preparation of bicyclic compounds as partyl protease and β secretase inhibitors for treating conditions associated withamyloidosis such as Alzheimer's disease, PCT Int. Appl., 2005087714, 22 Sep2005); The report of chroman-4-amine could not be seen

Method used

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  • Reductive amination and resolution of isochroman-4-one

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Embodiment 1

[0006] 1) Preparation of isochroman-4-amine

[0007] In a 1000ml autoclave, add 74g isochroman-4-one, 700ml absolute ethanol and 11g catalyst SN-600P, seal the reaction kettle, use a vacuum pump to remove the air in the kettle, and then fill it with nitrogen to 0.5MPa, and then use a vacuum pump to remove the air in the kettle. Evacuate with a vacuum pump; fill with 44g of ammonia gas under negative pressure. After filling the ammonia gas, fill the autoclave with hydrogen to 4.0MPa, and raise the temperature to 95°C for reaction. After reacting for 9 hours, it was found that the hydrogen pressure did not drop any more, so the reaction was stopped. After the temperature of the system dropped to room temperature, the reaction liquid was filtered and concentrated to obtain crude isochroman-4-amine. Add the crude product to dilute hydrochloric acid solution while stirring, let it react to form isochroman-4-amine hydrochloride, and dissolve it in the aqueous solution, and extract ...

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Abstract

The invention discloses a method for preparation of isochroman-4-amine from isochroman-4-one through reductive amination and further dynamic resolution of isochroman-4-amine for preparation of R-isochroman-4-amine. The method provided by the invention has the advantages of simple operation, usage of easily available raw materials, good product yield, high optical purity of the products, etc.

Description

technical field [0001] The invention relates to a synthesis and resolution method of chiral amines, in particular to a method for preparing isochroman-4-amine by reductive amination of isochroman-4-one and further performing dynamic kinetic resolution. Background technique [0002] Isochroman-4-one as a latent chiral intermediate. In the existing related research, the method of how to prepare isochroman-4-amine is mainly to first use sodium borohydride to make isochroman-4-alcohol, then in toluene solvent with diphenylphosphoric azide and DBU reaction (Preparation of bicyclic compounds as partyl protease and β secretase inhibitors for treating conditions associated withamyloidosis such as Alzheimer's disease, PCT Int. Appl., 2005087714, 22 Sep2005); The report of chroman-4-amine cannot be seen. Contents of the invention [0003] The present invention aims to provide a simple and easy-to-operate method for preparing isochroman-4-amine from isochroman-4-one, and then to sp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/76
CPCC07D311/76
Inventor 王际菊
Owner 王际菊