Beckmann rearrangement of 3-aza-a-homo-4α-androsten-4,17-dione oxime and 3-oxo-13α-amino-13,17-seco-4-androsten-17-oic 13,17-lactam oxime

Rearrangements of 3-aza-A-homo-4α-androsten-4, 17-dione oxime produced a mixture of the normal lactam product and the product of a “second order” cleavage, an unsaturated nitrile. The lactam 3, 17α-di-aza-A, D-bishomoandrost-4α-ene-4, 17-dione was also obtained from the rearrangement of the syn-3-oxo-13α-amino-13, 17-seco-4-androsten-17-oic-13, 17-lactam oxime. The resolution of syn- and anti-isomers of VIII was effected by column chromatography and their structure was determined by spectral data.