hydrogen; palladium on activated charcoal in methanol; acetic acid P=2585.7 Torr; 6 h;

1: 75 percent / KOH / H2O / 5 h / Heating 2: 93 percent / NaBH4 / ethanol / 1.) room temperature, 18 h, 2.) reflux, 1 h 3: 96 percent / PBr3 / tetrahydrofuran / 1.5 h / 0 °C 4: t-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) -100 deg C, 4 h 5: hydrazine, acetic acid / ethanol; H2O / 2 h / Ambient temperature 6: K2CO3 / acetone / 14 h / Heating 7: lithium aluminum hydride / tetrahydrofuran / Heating 8: 0.026 g / hydrogen / 10percent Pd/C / acetic acid; methanol / 6 h / 2585.7 Torr View Scheme

1: 73 percent / ammonium acetate / 1.5 h / Heating 2: 55 percent / lithium aluminum hydride / diethyl ether; tetrahydrofuran / 1.) reflux, 2 h, 2.) room temperature, overnight 3: formic acid / 48 h / 50 °C 4: 88 percent / ammonium sulfate / toluene / 48 h / Heating 5: t-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) -100 deg C, 4 h 6: hydrazine, acetic acid / ethanol; H2O / 2 h / Ambient temperature 7: K2CO3 / acetone / 14 h / Heating 8: lithium aluminum hydride / tetrahydrofuran / Heating 9: 0.026 g / hydrogen / 10percent Pd/C / acetic acid; methanol / 6 h / 2585.7 Torr View Scheme

1: formic acid / 48 h / 50 °C 2: 88 percent / ammonium sulfate / toluene / 48 h / Heating 3: t-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) -100 deg C, 4 h 4: hydrazine, acetic acid / ethanol; H2O / 2 h / Ambient temperature 5: K2CO3 / acetone / 14 h / Heating 6: lithium aluminum hydride / tetrahydrofuran / Heating 7: 0.026 g / hydrogen / 10percent Pd/C / acetic acid; methanol / 6 h / 2585.7 Torr View Scheme

1: 96 percent / PBr3 / tetrahydrofuran / 1.5 h / 0 °C 2: t-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) -100 deg C, 4 h 3: hydrazine, acetic acid / ethanol; H2O / 2 h / Ambient temperature 4: K2CO3 / acetone / 14 h / Heating 5: lithium aluminum hydride / tetrahydrofuran / Heating 6: 0.026 g / hydrogen / 10percent Pd/C / acetic acid; methanol / 6 h / 2585.7 Torr View Scheme

1: 55 percent / lithium aluminum hydride / diethyl ether; tetrahydrofuran / 1.) reflux, 2 h, 2.) room temperature, overnight 2: formic acid / 48 h / 50 °C 3: 88 percent / ammonium sulfate / toluene / 48 h / Heating 4: t-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) -100 deg C, 4 h 5: hydrazine, acetic acid / ethanol; H2O / 2 h / Ambient temperature 6: K2CO3 / acetone / 14 h / Heating 7: lithium aluminum hydride / tetrahydrofuran / Heating 8: 0.026 g / hydrogen / 10percent Pd/C / acetic acid; methanol / 6 h / 2585.7 Torr View Scheme

1: t-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) -100 deg C, 4 h 2: hydrazine, acetic acid / ethanol; H2O / 2 h / Ambient temperature 3: K2CO3 / acetone / 14 h / Heating 4: lithium aluminum hydride / tetrahydrofuran / Heating 5: 0.026 g / hydrogen / 10percent Pd/C / acetic acid; methanol / 6 h / 2585.7 Torr View Scheme

1: 88 percent / K2CO3 / ethanol 2: 73 percent / ammonium acetate / 1.5 h / Heating 3: 55 percent / lithium aluminum hydride / diethyl ether; tetrahydrofuran / 1.) reflux, 2 h, 2.) room temperature, overnight 4: formic acid / 48 h / 50 °C 5: 88 percent / ammonium sulfate / toluene / 48 h / Heating 6: t-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) -100 deg C, 4 h 7: hydrazine, acetic acid / ethanol; H2O / 2 h / Ambient temperature 8: K2CO3 / acetone / 14 h / Heating 9: lithium aluminum hydride / tetrahydrofuran / Heating 10: 0.026 g / hydrogen / 10percent Pd/C / acetic acid; methanol / 6 h / 2585.7 Torr View Scheme

1: t-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) -100 deg C, 4 h 2: hydrazine, acetic acid / ethanol; H2O / 2 h / Ambient temperature 3: K2CO3 / acetone / 14 h / Heating 4: lithium aluminum hydride / tetrahydrofuran / Heating 5: 0.026 g / hydrogen / 10percent Pd/C / acetic acid; methanol / 6 h / 2585.7 Torr View Scheme

1: K2CO3 / acetone / 14 h / Heating 2: lithium aluminum hydride / tetrahydrofuran / Heating 3: 0.026 g / hydrogen / 10percent Pd/C / acetic acid; methanol / 6 h / 2585.7 Torr View Scheme