1H NMR study of the hydrolysis of N-acylhydroxy[2H]methylpyrroles
Abstract
KOH catalysed hydrolysis of the (S)- and (R)-N- (N-phthalylleucinyl)hydroxy[2H]methylpyrroles 6b and 6c, in CD3CN containing 1 equiv. of (+)-sec-butylamine, proceeds by an initial N- to O-acyl transfer with retention of configuration at the labelled centre, followed by trapping of an azafulvene to give (S)- and (R)-sec-butylamino[2H]methylpyrroles 9b.