hydrogen; palladium on activated charcoal in methanol P=760 Torr;

lithium aluminium tetrahydride in tetrahydrofuran

1: 26 percent / NaH / tetrahydrofuran / 18 h / 65 °C 2: 95 percent / H2 / Pd-C / methanol / 760 Torr View Scheme

1: 90 percent / triethylamine; 4-dimethylaminopyridine / CH2Cl2 / 0.5 h / 20 °C 2: 26 percent / NaH / tetrahydrofuran / 18 h / 65 °C 3: 95 percent / H2 / Pd-C / methanol / 760 Torr View Scheme