Process for the synthesis of vincadifformine and related derivatives
US4267330A · kind A · utility
Assignee
Inventor
Key dates
| Filing date | Aug 24, 1978 |
| Grant date | May 12, 1981 |
| Priority date | — |
| Expiry date | Aug 24, 1998 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D487/04
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
This invention relates to the preparation of vincadifformine and related derivatives which are useful as starting material for the synthesis of vincamine and other related compounds possessing interesting psychopharmacologic properties. A N-benzyl-tetrahydro-.gamma.-carboline compound (III) is halogenated with t-butyl hypochlorite to obtain a haloindolenine compound which is directly treated with a metal dialkyl malonate such as thallium dialkyl malonate to provide a dialkyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino (4,5-b) indole-5,5-dicarboxylate compound, said latter compound being hydrogenated to provide a dialkyl 1,2,3,4,5,6 hexahydroazepino (4,5-b) indole-5,5-dicarboxylate, said latter compound being condensed with a functionalized aldehyde, typically a haloaldehyde, to provide vincadifformine or a related derivative by passing through an intermediate compound being a salt of a dialkyl 3,3-(alkenyl)-1,2,3,4,5,6-hexahydroazepino(4,5-b) indolinium-(5,5)-dicarboxylate.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.