Preparation method for R-6-hydroxy-1-aminoindan

A technology of aminoindane and R-6-, which is applied in the field of separation and preparation of optical pure chiral compounds, can solve the problems of separation and preparation of R-6-hydroxyl-1-aminoindene, etc., and achieve complete utilization of raw materials, optical The effect of high purity and simple operation

Active Publication Date: 2015-12-23
陈永军
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

It can be found through the research literature that there is no information about how to use kinetics and dynamic kinetics to resolve and prepare R-6-hydroxyl-1-aminoindan

Method used

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  • Preparation method for R-6-hydroxy-1-aminoindan

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Effect test

Embodiment 1

[0008] 1. Resolution of 6-hydroxy-1-aminoindan

[0009] In a 1000ML autoclave, add 500ML toluene, 74.5G 6-hydroxy-1-aminoindan, 90.2g R-1-styryl acetate, 6g Candida antarctica lipase B and 10g Raney nickel, seal the autoclave , replace the air in the autoclave with nitrogen, and then pass hydrogen into the autoclave to a pressure of 1.0MP, start stirring, and raise the temperature to 50°C for reaction; after 18 hours, take a sample to detect that 6-hydroxy-1-aminoindane is completely Converted to the acetyl compound of R-6-hydroxyl-1-aminoindan; after the reaction, the solution was concentrated and subjected to column chromatography to obtain 90.2 g of the pure R-6-hydroxyl-1-aminoindan acetyl compound , the yield is 95.5%.

[0010] 2. Acid hydrolysis to obtain R-6-hydroxy-1-aminoindan salt

[0011] Take 95.5 g of the acetyl compound of R-6-hydroxy-1-aminoindane obtained by repeating the previous step several times and add it to 1000 ml of ethanol and concentrated hydrochlor...

Embodiment 2

[0015] 1. Resolution of 6-hydroxy-1-aminoindan

[0016] In a 1000ML autoclave, add 500ML n-hexane, 74.5G 6-hydroxy-1-aminoindan, 100g R-1-styroyl acetate, 7g Candida plicata lipase and 14g Raney nickel in sequence, and seal the autoclave , replace the air in the autoclave with nitrogen, then pass hydrogen into the autoclave to a pressure of 1.5MP, start stirring, and raise the temperature to 40°C for reaction; after 15 hours, take a sample for detection, 6-hydroxy-1-aminoindane Completely converted into the acetyl compound of R-6-hydroxyl-1-aminoindan; after the reaction, the solution was concentrated and subjected to column chromatography to obtain 91.8g of the acetyl compound of R-6-hydroxyl-1-aminoindan , the yield is 96.1%.

[0017] 2. Acid hydrolysis to obtain R-6-hydroxy-1-aminoindan salt

[0018] Take 95.5 g of the acetyl compound of R-6-hydroxy-1-aminoindane obtained by repeating the previous step several times and add it to a solution mixed with 1000 ml of ethanol a...

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Abstract

The invention discloses a method for preparing R-6-hydroxy-1-aminoindan through biocatalytic dynamic kinetic resolution. The method comprises the following concrete steps: in an autoclave, allowing Candida antarctica Lipase B to catalyze transesterification reaction of 6-hydroxy-1-aminoindan with R-1-styracitol acetate so as to produce an R-6-hydroxy-1-aminoindan acyl compound and introducing Raney nickel as a racemization catalyst at the same time so as to guarantee complete conversion of 6-hydroxy-1-aminoindan into R-6-hydroxy-1-aminoindan; and hydrolyzing the obtained acyl compound so as to obtain R-6-hydroxy-1-aminoindan with an ee value of more than 99%. The method is simple to operate; raw materials are completely utilized; prepared R-6-hydroxy-1-aminoindan has high optical purity; and the method has great guidance and application values in production and preparation of R-6-hydroxy-1-aminoindan.

Description

technical field [0001] The invention relates to a method for the resolution and preparation of optically pure chiral compounds, in particular to a method for the preparation of R-6-hydroxyl-1-aminoindan by dynamic kinetic resolution. Background technique [0002] R-6-hydroxy-1-aminoindan as a chiral intermediate. In the existing related research, there are few reports on how to prepare optically pure R-6-hydroxy-1-aminoindan. It can be found through the research literature that there is no information on how to prepare R-6-hydroxyl-1-aminoindan by kinetic and dynamic kinetic resolution. The present invention uses Candida antarctica lipase B as the resolution catalyst, Raney nickel as the racemization catalyst, and successfully realizes dynamic kinetic resolution to prepare R- 6-hydroxyl-1-aminoindan, and the final product has good yield and high purity. Contents of the invention [0003] In order to solve the above problems, the present invention proposes dynamic kineti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P41/00C12P13/00C07C211/42C07C209/62
Inventor 陈永军
Owner 陈永军
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