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A simple convenient synthesis of trans ‐1,2,3,4,4a,5,6,10b‐octahydrophenanthridines
Author(s) -
Rahman M. F.,
May Everette L.
Publication year - 1976
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570130638
Subject(s) - chemistry , yield (engineering) , acetic acid , ethyl chloroformate , ethanol , amine gas treating , organic chemistry , medicinal chemistry , metallurgy , materials science
Abstract trans ‐1,2,3,4,4a,5,6,10b‐Octahydrophenanthridine, the 9‐methoxy analog, and 5‐methyl derivatives ( 6a,6b ) of each have been synthesized from trans ‐phenylcyclohexylamines ( 2a,2b ) and ethyl chloroformate followed by cyclization and reduction or by cyclization, N ‐methylation and reduction. The oximes ( la,1b ) of 2‐phenylcyclohexanone and the m ‐methoxy relative, a mixture of the syn and anti isomers, were reduced to 2a and 2b with sodium and ethanol. Hydrogenation (platinum oxide‐acetic acid) of 1a gave in addition to 2a , a small yield of 2‐cyclohexylcyclohexyl‐amine. Similar hydrogenation of 1b gave only this fully reduced compound.