Synthesis of c-17 trans β-lactams of the androstane series

3,3′-Ethylenedioxyandrost-4-en-17β-ol 1 was converted into the ethyl ester 2 by reaction with potassium metal and ethyl chloroacetate. The ethyl ester 2 on reaction with hydrazine gave the hydrazide 3 . Condensation of 3 with aryl aldehydes gave the Schiff bases 4 . The reaction of Schiff bases 4 with mono-chloroacetyl chloride in the presence of triethylamine afforded the β-lactams 5 .