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.