Process for producing trans-4-amino-1-cyclohexanecarboxylic acid derivative

By reacting a base with cis-4-amino-1-cyclohexanecarboxylic acid in an aprotic solvent, the isomerization rate is increased, and the trans isomer is obtained in high yield through a recrystallization step, solving the current problem. The problem of low yield of trans isomer in the technology has been solved, and the efficient production of drug intermediates has been achieved.

CN1821217AInactive Publication Date: 2006-08-23SHIONOGI & CO LTD
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Patent Information

Application Number
CN200610059627.X
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Priority Date
2002-03-12
Filing Date
2003-03-07
Publication Date
2006-08-23
Estimated Expiration
Not applicable · inactive patent

AI Technical Summary

Technical Problem

It is difficult to effectively produce trans-4-amino-1-cyclohexanecarboxylic acid derivatives with the existing technology, especially due to the low yield of the trans-isomer, which makes it difficult to mass-produce it as a pharmaceutical intermediate.

Method used

By reacting the base with cis-4-amino-1-cyclohexanecarboxylic acid in an aprotic solvent, the isomerization rate is significantly increased and the trans isomer is obtained in high yields via a recrystallization step.

Benefits of technology

The efficient preparation of trans-4-amino-1-cyclohexanecarboxylic acid derivatives is achieved, with an isomerization rate of 90% or higher, and is suitable for the production of pharmaceutical intermediates.

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Abstract

A process for the preparation of Compound (I) comprising reacting Compound (II) with a base in an aprotic solvent, which is represented by the following scheme: wherein R<1> and R<2> are each independently lower alkyl.
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