Process for making perhydroindole-2-carbonxylic acid
US4879392A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Oct 21, 1987 |
| Grant date | Nov 7, 1989 |
| Priority date | — |
| Expiry date | Oct 21, 2007 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D209/42
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A process for the asymmetric preparation of a compound of the formula ##STR1## wherein the hydrogen at 3a and 7a are of cis or trans configuration and their non-toxic, pharmaceutically acceptable acid addition salts comprising submitting a compound of the formula ##STR2## to a Hoffman reaction and reacting the resulting product with formaldehyde in the presence of cyanide ions and acid halide of benzoic acid or an aliphatic carboxylic acid of 1 to 5 carbon atoms to obtain a compound of the formula ##STR3## wherein R is acyl of benzoic acid or aliphatic carboxylic acid of 1 to 5 carbon atoms, cyclizing the latter to form a compound of the formula ##STR4## selectively hydrolyzing the latter with a dilute aqueous mineral acid to obtain a compound of the formula ##STR5## subjecting the latter to hydrolysis with a concentrated aqueous mineral acid to form the acid addition salt of a compound of claim 1 and optionally forming the free base.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.