hydrogen; palladium oxide on charcoal in ethanol; water

in ammonia; acetone

1: 72.6 percent / N-methyl-2-pyrrolidone / 4.5 h / Heating 2: 45 percent / AcOH, Ac2O / 15 h / Heating 3: 40.5 percent / diphenylphosphonic azide (DPPA), Et3N / 2-methyl-propan-2-ol / 9 h / Heating 4: 7 percent / 30percent aq. H2O2 / methanol; tetrahydrofuran / 0.25 h / 15 °C View Scheme

1: 45 percent / AcOH, Ac2O / 15 h / Heating 2: 40.5 percent / diphenylphosphonic azide (DPPA), Et3N / 2-methyl-propan-2-ol / 9 h / Heating 3: 7 percent / 30percent aq. H2O2 / methanol; tetrahydrofuran / 0.25 h / 15 °C View Scheme

1: dimethylformamide / 8 h / 130 °C 2: NaBH4 / bis-(2-methoxy-ethyl) ether; propan-2-ol / 2 h / Heating 3: 80percent aq. hydrazine hydrate / ethanol / 3 h / Heating 4: 7 percent / 30percent aq. H2O2 / methanol; tetrahydrofuran / 0.25 h / 15 °C View Scheme

1: 40.5 percent / diphenylphosphonic azide (DPPA), Et3N / 2-methyl-propan-2-ol / 9 h / Heating 2: 7 percent / 30percent aq. H2O2 / methanol; tetrahydrofuran / 0.25 h / 15 °C View Scheme

1: 80percent aq. hydrazine hydrate / ethanol / 3 h / Heating 2: 7 percent / 30percent aq. H2O2 / methanol; tetrahydrofuran / 0.25 h / 15 °C View Scheme

1: NaBH4 / bis-(2-methoxy-ethyl) ether; propan-2-ol / 2 h / Heating 2: 80percent aq. hydrazine hydrate / ethanol / 3 h / Heating 3: 7 percent / 30percent aq. H2O2 / methanol; tetrahydrofuran / 0.25 h / 15 °C View Scheme