Process for producing optically active tropinonemonocarboxylic acid derivative
US6486323B1 · kind B1 · utility
Assignee
Inventors
Key dates
| Filing date | Mar 30, 2001 |
| Grant date | Nov 26, 2002 |
| Priority date | — |
| Expiry date | Mar 30, 2021 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC12P41/005
- WIPO fieldBiotechnology
- WIPO sectorChemistry
Abstract
An optically active tropinonemonocarboxylic acid ester derivative useful as an intermediate for synthesis of optically active tropane derivatives was obtained by reacting succindialdehyde with an organic amine and acetonedicarboxylic acid ester to obtain a tropinonedicarboxylic acid ester derivative, and then subjecting this derivative to enzyme-catalyzed asymmetric dealkoxy-carbonylation. Since anhydroecgonine methyl ester derived from the optically active tropinone-monocarboxylic acid ester derivative by reduction and dehydration had the same direction of optical rotation as in the case of anhydroecgonine methyl ester obtained from natural cocaine, it was proved that the obtained optically active tropinonemonocarboxylic acid ester derivative had the same absolute configuration as that of natural cocaine. The yield of the optically active tropinonemonocarboxylic acid ester derivative from the asymmetric dealkoxycarbonylation was 30 to 50 mol %, and its optical purity was 70 to 97% ee. In addition, it was found that a crystalline optically active anhydroecgonine carboxylic acid ester derivative can be obtained by reducing and then dehydrating the optically active tropinonemonocarbo…
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.