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Preparation of r-6-Hydroxy-1-aminoindan by Dynamic Kinetic Resolution

A dynamic kinetics, R-6- technology, which is applied in the field of dynamic kinetics splitting and preparing R-6-hydroxy-1-aminoindane, can solve the problem of splitting and preparing R-6-hydroxy-1-aminoindene, etc. problem, to achieve the effect of complete utilization of raw materials, high optical purity and simple operation

Active Publication Date: 2018-09-14
陈永军
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 of r-6-Hydroxy-1-aminoindan by Dynamic Kinetic Resolution

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0008] In a 1000ML autoclave, add 500ML toluene, 74.5G 6-hydroxy-1-aminoindan, 115.9g D-(-)-O-acetylmandelic acid, 6g Candida plicata lipase and 10g KT-02, seal the high pressure In the autoclave, replace the air in the autoclave with nitrogen, then pass hydrogen into the autoclave to a pressure of 1.0MP, start stirring, and heat up to 50°C for reaction; after 19 hours, take a sample for detection, 6-hydroxy-1-aminoindane Completely converted to the acetyl compound of R-6-hydroxyl-1-aminoindane; after the reaction, the solution was concentrated and subjected to column chromatography to obtain the acetyl compound 90.8 of pure R-6-hydroxyl-1-aminoindane g, the yield is 95.1%.

[0009] 2. Acid hydrolysis to obtain R-6-hydroxy-1-aminoindan

[0010] 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 hydrochloric acid...

Embodiment 2

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

[0015] In a 1000ML autoclave, add 500ML toluene, 74.5G6-hydroxy-1-aminoindan, 144.9g D-(-)-O-acetylmandelic acid, 7g Candida plicata lipase and 13g KT-02 in sequence, 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 70°C for reaction; after 13 hours, sample detection, 6-hydroxy-1-amino Indane is completely converted into the acetyl compound of R-6-hydroxyl-1-aminoindane; after the reaction, the solution is concentrated and subjected to column chromatography to obtain the acetyl compound of R-6-hydroxyl-1-aminoindane 90.4g, the yield is 94.7%.

[0016] 2. Acid hydrolysis to obtain R-6-hydroxy-1-aminoindan salt

[0017] 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 and concentrated su...

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Abstract

The invention relates to a method for preparing R-6-hydroxy-1-aminoindane through dynamic kinetic resolution. The method is characterized by using candida rugosa lipase as a biological resolution catalyst, D-(-)-O-acetyl mandelic acid as an acyl donor and a non-crystal nickel catalyst KT-02 as a racemization catalyst to carry out one-pot dynamic kinetic resolution reaction in an autoclave in the presence of hydrogen to convert 6-hydroxy-1-aminoindane to an R-6-hydroxy-1-aminoindane acyl compound and carrying out acid hydrolysis, alkali freeing, and the like on the acyl compound to obtain R-6-hydroxy-1-aminoindane with ee (enantiomeric excess) value more than 99%. The method has the characteristics of simplicity in operation, cheap and accessible racemization catalyst, complete utilization of the raw materials, high optical purity of the product, and the like, and has great guidance and application values in production and preparation of R-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 the preparation of R-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. R-6-hydroxyl-1-aminoindan is one of the important chiral pharmaceutical intermediates. In the existing related research, there is little information on how to prepare optically pure R-6-hydroxyl-1-aminoindan. reports. 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 plicate lipase as the resolution catalyst, KT-02 as the racemization catalyst, and successfully realizes dy...

Claims

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Application Information

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