The stereoselective borohydride/H+ reduction of the C-(5) - C-(6) doub
le bond in Delta(5)-3-oxo-4-azasteroids has been studied. The intermed
iate acylimine is preferentially attacked by borohydride from the a si
de. The optimization with respect to the type of borohydride, solvent,
catalyst and temperature has been carried out.