hydrogen; palladium on activated charcoal in methanol

1: 99 percent / pyridine / cooling 2: 98.5 percent / NaN3 / dimethylformamide / 8 h / 70 °C 3: H2 / Raney Nickel / methanol; H2O / 1.5 h / 2068.59 Torr 4: 3.17 g / Et3N / dimethylsulfoxide / 8 h 5: 70 percent / LiBH4 / tetrahydrofuran / 3.5 h 6: H2 / Pd-C / methanol / 7 h / 3102.89 Torr View Scheme

1: H2 / Raney Nickel / methanol; H2O / 1.5 h / 2068.59 Torr 2: 3.17 g / Et3N / dimethylsulfoxide / 8 h 3: 70 percent / LiBH4 / tetrahydrofuran / 3.5 h 4: H2 / Pd-C / methanol / 7 h / 3102.89 Torr View Scheme

1: 98.5 percent / NaN3 / dimethylformamide / 8 h / 70 °C 2: H2 / Raney Nickel / methanol; H2O / 1.5 h / 2068.59 Torr 3: 3.17 g / Et3N / dimethylsulfoxide / 8 h 4: 70 percent / LiBH4 / tetrahydrofuran / 3.5 h 5: H2 / Pd-C / methanol / 7 h / 3102.89 Torr View Scheme

1: 3.17 g / Et3N / dimethylsulfoxide / 8 h 2: 70 percent / LiBH4 / tetrahydrofuran / 3.5 h 3: H2 / Pd-C / methanol / 7 h / 3102.89 Torr View Scheme

1: 70 percent / LiBH4 / tetrahydrofuran / 3.5 h 2: H2 / Pd-C / methanol / 7 h / 3102.89 Torr View Scheme

1: NaHCO3 / H2O; dioxane 2: thionyl chloride 3: pyridine 4: sodium azide / dimethylformamide / 70 °C 5: hydrogen; Raney nickel / methanol 6: triethylamine / dimethylsulfoxide / 50 °C 7: LiBH4 / tetrahydrofuran 8: hydrogen / Pd-C / methanol View Scheme

1: thionyl chloride 2: pyridine 3: sodium azide / dimethylformamide / 70 °C 4: hydrogen; Raney nickel / methanol 5: triethylamine / dimethylsulfoxide / 50 °C 6: LiBH4 / tetrahydrofuran 7: hydrogen / Pd-C / methanol View Scheme