Process for the preparation of 15-hydroxyimino-E-homoeburnane and intermediates therefor
US4314939A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Jul 14, 1980 |
| Grant date | Feb 9, 1982 |
| Priority date | — |
| Expiry date | Jul 14, 2000 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D471/22
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A process for the preparation of 15-hydroxyimino-E-homoeburnane derivatives of the formula (I), ##STR1## wherein X.sup.1 stands for hydrogen or halogen and PA1 R is a C.sub.1-6 alkyl group, or acid addition salts and optically active derivatives thereof. These compounds are valuable intermediates of the synthesis of compounds with outstanding biological effects. According to the invention a racemic or optically active 15-hydroxy-E-homoeburnane derivative of the formula (II), ##STR2## is treated, optionally after separating the 15-epimers and/or resolution, with a halogenating agent. The resulting 15-halo-E-homoeburnane derivative of the formula (III), ##STR3## wherein X.sup.2 stands for halogen, is reacted, optionally after separating the 15 epimers and/or resolution, with an alkali nitrite in the presence of an acid, and, if desired, the resulting 15-hydroxyimino-E-homoeburnane derivative of the formula (I) is converted into its acid addition salt and/or resolved. The compounds of the formula (III) formed as intermediates in the above process are new and biologically active.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.