Preparation of useful intermediates of dextrorphan
Passarotti, C. M.; Valenti, M.; Grianti, M.
Boll.Chim.Farm. 1993, 132: 11 472-474
Dextrorphan is the main metabolite of Dextromethorphan, a drug with high anti-tussive activity.In this preliminary work we report on the synthesis of two essential intermediates for its preparation: 2-(1-cyclohexenyl)ethyl amine and (R;S)-1-(4-methoxy-benzyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline.KEY-WORDS: Dextrorphan-intermediates; Alcohol-dehydration; LiAlH4-reduction; NaBH4-reduction; C-alkylation 2-(1-cyclohexenyl)ethylamine; 1,2,3,4,5,6,7,8-octahydroisoquinoline-derivatives; Nitrile reduction to primary amine
you can use 2-(1-cyclohexenyl)ethyl amine in place of the dihydro phenethylamine. i think this can be prepared from cyclohexanone starting with a grignard. the above ref is from the belstein databases - perhaps some kind bee with access to the complete article could post it or alternatively pm blondie.