Azido-deca:hydro-hydroxyphenyl-methyl-isoquinoline isomer - useful as analgesic and CNS depressant

摘要

(4a, RS, 6SR, 8aRs)-6-Azido-decahydro-4-a(3-hydroxypheny l)-2-methyl-cis-isoquinoline of formula (I) is new. (I) is an analgesic which, unlike the (4aRS, 6RS, 8aRS) isomer, also acts as a morphine antagonist. It also has antidepressant, tranquillising and hypnotic activity. (I) is prepd. by reductive methylation of (4aRS, 6SR, 8aRS)-6-azido-decahydro-4a-(3-hydroxyphenyl)-cis-isoquinoline (II), which can be prepd. by reducing 2-benzoyl-octahydro-8a-(3-methoypheny l)-cis-6(2H)-isoquinolinone with NaBH4, sepg. the resulting isomers by TLC, and debenzoylating the 6SR isomer.