sulfuric acid in water T=95 - 100°C;

hydrazine in methanol

ammonium acetate; cyano-borane; compound with lithium hydride in ethanol

in tetrahydrofuran

1: 88 percent / pyridine / Ambient temperature 2: sodium azide / dimethylsulfoxide / 24 h / 100 °C 3: 52 percent / H2 / 10percent Pd/C / methanol / 24 h / 3102.9 Torr / Ambient temperature View Scheme

1: sodium azide / dimethylsulfoxide / 24 h / 100 °C 2: 52 percent / H2 / 10percent Pd/C / methanol / 24 h / 3102.9 Torr / Ambient temperature View Scheme

1.1: magnesium sulfate / dichloromethane / 2 h / 20 °C 1.2: 4 h / 110 °C 2.1: trifluoroacetic acid / acetone / 24 h / 65 °C 3.1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere 4.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 5.1: sodium azide / 24 h 6.1: 10 palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C View Scheme

1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / |Reflux 2: sulfuric acid / water / 95 - 100 °C View Scheme

1.1: magnesium sulfate / dichloromethane / 2 h / 20 °C 1.2: 4 h / 110 °C 2.1: trifluoroacetic acid / acetone / 24 h / 65 °C 3.1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere 4.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 5.1: sodium azide / 24 h 6.1: 10 palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C View Scheme

1: trifluoroacetic acid / acetone / 24 h / 65 °C 2: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere 3: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 4: sodium azide / 24 h 5: 10 palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C View Scheme