Hydrogenolysis of 3-(benzyloxy) cyclophosphamide (10) using Pd/C catalyst and ethyl acetate as solvent leads to the formation of 3-hydroxycyclophosphamide (3,-20%) and cyclophosphamide (1,-10%), accompanied by regioselective hydrogen-exchange reactions at the C-4 and C-5 positions in 3 and 1. A variety of oxidizing reagents and liver microsomal incubation failed to provide evidence NMR) for conversion of 1 into 3, whereas identical ...