1: H2 / Pd-C 2: benzoyl peroxide 3: HCl / acetonitrile 4: N-iodosuccinimide, 4 Angstroem sieves / CH2Cl2; tetrahydrofuran 5: H2 / Pd-C / ethyl acetate / 2.5 h / 3102.9 Torr / Ambient temperature 6: bovine intestinal alkaline phosphatase 7: benzoyl peroxide / acetonitrile / 2 h / 0 °C 8: N-iodosuccinimide, 4 Angstroem sieves / CH2Cl2; tetrahydrofuran 9: H2 / Pd-C / ethyl acetate / 2.5 h / 3102.9 Torr / Ambient temperature 10: bovine intestinal alkaline phosphatase, or incubation in mouse plasma at 37 deg C View Scheme

1: 21 percent / dimethylaminopyridine / acetonitrile / 24 h / Ambient temperature 2: 75 percent Turnov. / Mg(OMe)2 / methanol / 0.75 h / Ambient temperature 3: 91 percent / HF-pyridine / tetrahydrofuran / 2 h / Ambient temperature View Scheme

1: 21 percent / dimethylaminopyridine / acetonitrile / 24 h / Ambient temperature 2: 75 percent Turnov. / Mg(OMe)2 / methanol / 0.75 h / Ambient temperature 3: 91 percent / HF-pyridine / tetrahydrofuran / 2 h / Ambient temperature 4: 75 percent / H2O2, NaHCO3 / tetrahydrofuran / 16 h / Ambient temperature View Scheme

hydrogen; palladium on activated charcoal in ethyl acetate 4 h;