Method for preparing (1R, 2S)-2, 6-dimethyl-1-indene amine by adopting chiral amino acid resolving agent

By using chiral amino acid derivatives as the splitting agent, the trans 2,6-dimethyl-1-indenamine is resolved, and the problems of inconvenience in use, yield and insufficient optical purity of chiral resolving agents in the prior art are solved, and the preparation of efficient and environmentally friendly (1R,2S)-2,6-dimethyl-1-indenamine is achieved, which is suitable for industrial production.

CN119661374AActive Publication Date: 2025-03-21DALIAN INSTITUTE OF CHEMICAL PHYSICS CHINESE ACADEMY OF SCIENCES
5 Cites 4 Cited by

Patent Information

Application Number
CN202311208661.9
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2023-09-19
Publication Date
2025-03-21
Estimated Expiration
2043-09-19

AI Technical Summary

Technical Problem

In the existing synthesis method of inderinsine fluoroxamide, the chiral resolving agent is inconvenient to use, the yield and optical purity are insufficient, and the process is complicated, making it difficult to achieve industrial production.

Method used

The racemic trans 2,6-dimethyl-1-indenamine was used as the splitting agent to resolve the chiral amino acid derivatives, and (1R,2S)-2,6-dimethyl-1-indenamine with high optical purity and high yield was prepared through specific solvents and conditions.

Benefits of technology

(1R,2S)-2,6-dimethyl-1-indenamine with high optical purity (ee value greater than 97%) and high yield (resolution yield greater than 95%) is achieved, and the resolving agent and solvent can be recycled and recycled. The process conditions are mild and suitable for industrial production.

✦ Generated by Eureka AI based on patent content.
Patent Text Reader

Abstract

The invention discloses a chiral amino acid resolving agent for preparing trans chiral indene amine, and particularly provides a chiral amino acid derivative which is used as a resolving agent for resolving trans-2, 6-dimethyl-1-indene amine and preparing (1R, 2S)-2, 6-dimethyl-1-indene amine. According to the method, the conditions of the resolution process are mild, the used solvent is a general solvent which is widely applied in the market, low in price and easy to obtain, and the (1R, 2S)-2, 6-dimethyl-1-indene amine is obtained with high yield and high optical purity. The method has the beneficial effects that (1R, 2S)-2, 6-dimethyl-1-indene amine is obtained, the ee value of the (1R, 2S)-2, 6-dimethyl-1-indene amine is greater than 97%, and the resolution yield is greater than 95%. As the resolving agent is poor in hydrophilicity, the resolving agent can be recycled at a high recovery rate, the process repeatability is high, and industrial production is easy to realize.
Need to check novelty before this filing date? Find Prior Art