Method for preparing (S)-6-hydroxy-1-aminoindane through dynamic kinetic resolution

A dynamic dynamics and aminoindane technology, which is applied in the preparation of organic compounds, the preparation of aminohydroxyl compounds, organic chemistry, etc., to achieve the effects of simple operation, high optical purity of products, and complete utilization of raw materials

Inactive Publication Date: 2015-11-04
SHANDONG PROVINCIAL HOSPITAL
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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

[0007] 1. Resolution of 6-hydroxy-1-aminoindan

[0008] In a 1000ML autoclave, sequentially add 500ML toluene, 74.5G 6-hydroxy-1-aminoindan, 115.9g L-(+)-O-acetylmandelic acid, 6g Candida plicata lipase and 10g KT-02, seal Autoclave, replace the air in the autoclave with nitrogen, then pass hydrogen into the autoclave to a pressure of 1.0MP, start stirring, and raise the temperature to 55°C for reaction; after 20 hours, sample detection, 6-hydroxyl-1-amino Indane is completely converted into the acetyl compound of (S)-6-hydroxyl-1-aminoindane; after the reaction, the solution is concentrated and subjected to column chromatography to obtain pure (S)-6-hydroxyl-1-aminoindane Full acetyl compound 90.3g, yield is 94.6%.

[0009] 2. Acid hydrolysis to obtain (S)-6-hydroxy-1-aminoindan salt

[0010] Get the acetyl compound 95.5g of (S)-6-hydroxyl-1-aminoindane that repeats the previous step to make several times and join in the solution that the ethanol of 1000ml and concentrated ...

Embodiment 2

[0014] 1. Resolution of 6-hydroxy-1-aminoindan

[0015] In a 1000ML autoclave, sequentially add 500ML toluene, 74.5G 6-hydroxy-1-aminoindan, 144.9g L-(+)-O-acetylmandelic acid, 7g Candida plicata lipase and 12g KT-02, seal 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 65°C for reaction; after 15 hours, sample detection, 6-hydroxy-1-amino Indane is completely converted into the acetyl compound of (S)-6-hydroxyl-1-aminoindane; after the reaction, the solution is concentrated and subjected to column chromatography to obtain pure (S)-6-hydroxyl-1-aminoindane The full acetyl compound was 88.9g, and the yield was 93.1%.

[0016] 2. Acid hydrolysis to obtain (S)-6-hydroxy-1-aminoindan salt

[0017] Get 95.5 g of the acetyl compound of (S)-6-hydroxyl-1-aminoindane that repeats the previous step to make several times and join in the solution that the ethanol of 1000...

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Abstract

The invention relates to a method for preparing (S)-6-hydroxy-1-aminoindane through dynamic kinetic resolution. According to the method, 6-hydroxy-1-aminoindane serves as the raw materials, fold candida lipase serves as a resolution catalyst, L-(+)-O-acetyl-Alpha-hydroxyphenylacetic acid serves as an acyl donor, KT-02 serves as a racemization catalyst, reaction is performed in a hydrogen environment, and the 6-hydroxy-1-aminoindane can be converted into an acetyl compound of the (S)-6-hydroxy-1-aminoindane. After the compound is purified, acid hydrolysis and alkali free operation are performed on the compound under the protection of nitrogen, then the (S)-6-hydroxy-1-aminoindane is obtained, and an ee value of the final product is above 99 percent. According to the method, the advantages that operation is easy, the racemization catalyst is low in price and easy to obtain, the raw materials can be completely utilized and the optical purity of the product is high are achieved, and great instruction and application value is achieved in the production preparation of the (S)-6-hydroxy-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 preparing (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. How to prepare optically pure S-6-hydroxy-1-aminoindan simply and conveniently becomes the problem to be solved by the present invention. C...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C215/64C07C213/10C07B57/00
Inventor 陈永军
Owner SHANDONG PROVINCIAL HOSPITAL
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