The two isomers (IIa and IIb) of 2-methyl-7-amino-cis-decahydroisoquinoline, which were obtained by catalytic hydrogenation of 2-methyl-7-amino-1, 2, 3, 4-tetrahydroisoquinoline (I), were also prepared from the corresponding decahydroisoquinolinols (IIIb and IIIa) via their tosylates. Deamination of IIa or IIb with nitrous acid was found to give a product which contained a mixture of alcohols (IIIa and IIIb) and the olefinic compounds (V and VI). Some mechanistic considerations were also presented for the deamination reaction.
