Preparation method of S-6-hydroxyl-1-aminoindane

A technology of aminoindane and S-6-, which is applied in the field of separation and preparation of optical pure chiral compounds, to achieve the effects of high optical purity of products, great guidance and application value, and complete utilization of raw materials

Pending Publication Date: 2015-10-28
陈永军
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

S-6-hydroxy-1-aminoindan is one of the important chiral pharmaceutical intermediates. In the existing 6-hydroxy-1-aminoindan related reports, how to prepare optically pure S-6- Hydroxy-1-aminoindan has rarely been reported

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0009] In a 1000ML autoclave, add 500ML toluene, 74.5G 6-hydroxy-1-aminoindan, 90.2g S-1-styryl acetate, 5g Candida plicata lipase and 10g Raney nickel, seal the autoclave, Replace the air in the autoclave with nitrogen, then feed hydrogen into the autoclave to a pressure of 1.5MP, start stirring, and raise the temperature to 45°C for reaction; after 19 hours, take a sample and detect that 6-hydroxy-1-aminoindane is completely converted It is the acetyl compound of S-6-hydroxyl-1-aminoindane; after the reaction is finished, the solution is concentrated and subjected to column chromatography to obtain 70.1 g of the acetyl compound of pure S-6-hydroxyl-1-aminoindane, The yield was 91.1%.

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

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

Embodiment 2

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

[0016] In a 1000ML autoclave, sequentially add 500ML toluene, 74.5G 6-hydroxy-1-aminoindan, 100g S-1-styroyl acetate, 7g Candida plicata lipase and 14g Raney nickel, seal the autoclave, Replace the air in the autoclave with nitrogen, then feed hydrogen into the autoclave to a pressure of 1.5MP, start stirring, and raise the temperature to 70°C for reaction; after 11 hours, take a sample to detect that 6-hydroxy-1-aminoindane is completely Converted to the acetyl compound of S-6-hydroxyl-1-aminoindan; after the reaction, the solution was concentrated and subjected to column chromatography to obtain 90.5 g of the acetyl compound of S-6-hydroxyl-1-aminoindan, The yield was 94.7%.

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

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

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PUM

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Abstract

The invention discloses a method for preparing S-6-hydroxyl-1-aminoindane with dynamic kinetic resolution. The method comprises steps as follows: 6-hydroxyl-1-aminoindane is taken as a raw material, Candida antarctica lipase B is taken as a resolution catalyst, S-1-methyl benzyl alcohol acetate is taken as an acyl donor, raney nickel is taken as a racemization catalyst, hydrogen gas is introduced into a high-pressure kettle for reaction, and 6-hydroxyl-1-aminoindane is completely transformed into an acetyl compound of S-6-hydroxyl-1-aminoindane; a reaction product is subjected to purification, acidolysis and the like, S-6-hydroxyl-1-aminoindane salt is obtained, the salt is subjected to alkalization, extraction, drying, concentration and the like, S-6-hydroxyl-1-aminoindane is obtained, and the ee value of the product is higher than 99%. The preparation method has the characteristics of cheap and available racemization catalyst, complete utilization of the raw material, high optical purity of the product and the like, and has great guidance and application value in production and preparation of S-6-hydroxyl-1-aminoindane.

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 S-6-hydroxyl-1-aminoindan by dynamic kinetic resolution. Background technique [0002] Indene compounds can be used as intermediates of medicines and pesticides. In recent years, many series of compound drugs and veterinary drugs based on indene have been developed at home and abroad. S-6-hydroxy-1-aminoindan is one of the important chiral pharmaceutical intermediates. In the existing 6-hydroxy-1-aminoindan related reports, how to prepare optically pure S-6- Hydroxy-1-aminoindan is rarely reported. It can be found through the research literature that the preparation of S-type compounds by kinetic and dynamic kinetic resolution is a technical problem for any product. The present invention uses the lipase Candida antarctica lipase B as the resolution catalyst, Raney nickel as the racemization catalys...

Claims

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Application Information

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