Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for preparing S-5-methyl-1-amino indan

A technology of aminoindan and S-5- is applied in the field of separation and preparation of optically 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: 2015-11-25
陈永军
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

S-5-methyl-1-aminoindane is one of the important chiral pharmaceutical intermediates. In the existing 5-methyl-1-aminoindane related reports, how to prepare optically pure S- 5-Methyl-1-aminoindan is rarely reported

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for preparing S-5-methyl-1-amino indan

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0008] 1. Resolution of 5-methyl-1-aminoindan

[0009] In a 1000ML autoclave, add 500ML toluene, 73.6G 5-methyl-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 5-methyl-1-aminoindane is completely Converted to the acetyl compound of S-5-methyl-1-aminoindane; after the reaction, the solution was concentrated and subjected to column chromatography to obtain pure acetyl compound of S-5-methyl-1-aminoindane 90.2g, the yield is 95.4%.

[0010] 2. Acid hydrolysis to obtain S-5-methyl-1-aminoindan salt

[0011] Take 994.6 g of the acetyl compound of S-5-methyl-1-aminoindane obtained by repeating the previous step several times and add it to the solution mixed with 1000 ml of ethanol and concentrated hydroch...

Embodiment 2

[0015] 1. Resolution of 5-methyl-1-aminoindan

[0016] In a 1000ML autoclave, add 500ML of toluene, 73.6G of 5-methyl-1-aminoindan, 100g of S-1-styroyl acetate, 7g of Candida plicata lipase and 14g of Raney nickel, and 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 for detection, 5-methyl-1-aminoindane Completely converted to the acetyl compound of S-5-methyl-1-aminoindane; after the reaction, the solution was concentrated and subjected to column chromatography to obtain the acetyl compound of S-5-methyl-1-aminoindane 89.0 g, the yield is 94.1%.

[0017] 2. Acid hydrolysis to obtain S-5-methyl-1-aminoindan salt

[0018] Take 94.6g of the acetyl compound of S-5-methyl-1-aminoindane obtained by repeating the previous step several times and add it to the solution mixed with 1000ml of ethanol and concentr...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a method for preparing S-5-methyl-1-amino indan by virtue of dynamic and kinetic resolution. The method comprises the steps of introducing hydrogen for reaction in an autoclave based on 5-methyl-1-amino indan as a raw material, candida antarctica lipase B as a resolution catalyst, S-1-styrallyl acetate as an acyle donor and raney nickel as a racemization catalyst so that 5-methyl-1-amino indan is completely transferred into an acetyl compound of S-5-methyl-1-amino indan; and performing purification, acidolysis and the like on a reaction product to obtain S-5-methyl-1-amino indan salt, and carrying out alkalization, extraction, drying, concentration and the like on the S-5-methyl-1-amino indan salt to obtain S-5-methyl-1-amino indan, wherein ee value of the product S-5-methyl-1-amino indan salt is larger than 99%. The method has the characteristics of cheap and easily available racemization catalyst, complete material utilization, high product optical purity and the like, and has extremely large guidance and application value in production and preparation of S-5-methyl-1-amino indan.

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-5-methyl-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-5-methyl-1-aminoindane is one of the important chiral pharmaceutical intermediates. In the existing 5-methyl-1-aminoindane related reports, how to prepare optically pure S- 5-methyl-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 catalyst, a...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C12P41/00C12P13/00C07C209/00C07C211/42
Inventor 陈永军
Owner 陈永军
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com