MONOAMINE OXIDASE-CATALYZED OXIDATIVE REARRANGEMENT OF ANS-1-(AMINOMETHYL)-2-METHOXY-3-PHENYLCYCLOPROPANE

ans-1-(Aminomethyl)-2-methoxy-3-phenylcyclopropane (3) was synthesized in three steps from (Z)-beta-methoxystyrene and ethyl diazoacetate. C ompound 3 was shown to be a substrate and inactivator of mitochondrial beef liver monoamine oxidase (MAO) with a partition ratio of 1428. MA O-catalyzed oxidation of 3 produces one major metabolite, isolated and identified by GCOSY, GHMQC, and GHMBC NMR techniques to be methoxy-3- phenyl-1-N-[(3-phenyl-N-pyrrolyl)methyl] cyclopropane (7). A mechanism , supported by a model reaction, is proposed for the formation of this metabolite.