Journal of the Chemical Society. Perkin transactions I p. 1091 - 1096 (1990)
Update date:2022-09-26
Topics:
Iddon, Brian
Yat, Patrick N.
The acetate of 5,6,7,8,9,10-hexahydro-6,9-methanobenzocyclo-octen-11-one (13) was reduced with zinc dust in a mixture of acetic acid and acetic anhydride, to give exclusively syn-11-acetamido-5,6,7,8,9,10-hexahydro-6,9-methanobenzocyclo-octene (3).By contrast, the acetate (17) of 6,7,8,9,10,11-hexahydro-7,10-methanocyclo-octa<1>benzothiophen-12-one oxime (16) gave a mixture of the syn- (6) (28percent yield) and anti-12-acetamido-derivatives (10) (25percent).The three amides (3), (6), and (10) were hydrolysed with acid to the corresponding amines (4), (7), and (11) andreduced with lithium aluminium hydride to the corresponding N-ethyl derivatives (5), (8), and (12) respectively.Reduction with sodium borohydride in methanol of 6,7,8,9,10,11-hexahydro-7,10-methanocyclo-octa<1>benzothiophen-12-one (15) gave exclusively the syn-alcohol (9). 11α-Acetamido-3,6-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine (1) was prepared by reduction in acetic acid-acetic anhydride of 3,6-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-11-one (19) oxime, prepared by adaptation of a procedure due to Belleau.
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