Synthesis of 1α and 1β-acylamino and alkylamino-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines and related compounds

The synthesis of series of 1α and 1β-alkylamino-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines from the corresponding acylamino intermediates is described. Cyclization of the 1β-chloromethylamido derivative 20 to the novel bridged benzomorphan 21 occurred whereas the corresponding 1β-chloromethylamido derivative 19 failed to cyclize for steric reasons. In addition several related 1α-acylamidomethyl- and 1β-alkyl-aminomethyl benzomorphans are reported.