N-ALKYLATION OF 17-AZASTEROIDS

N-Alkylation of 17-azasteroid lactams (16-oxo-17-azaandrost-5-en-3 bet a-ol acetate 3 and its D-homo analog 4) was studied. It has been found that both lactams are readily alkylated with iodomethane or iodoethan e. In contrast to this there was no reaction with 2-iodo-6-methylhepta ne due to the steric hindrance. 1,4-Addition of lactam to the conjugat ed systems was also studied. The addition to acrylonitrile proved to b e easy compared to crotononitrile. However the efficient addition to t he latter compound was also attained by using potassium t-butoxide as a base in t-butanol.