hydrogen; palladium on activated charcoal in ethanol P=2585.7 Torr;

palladium hydroxide on carbon; hydrogen in methanol T=20°C; P=2280.15 Torr; 15 h;

diborane in tetrahydrofuran; hexane 2 h; Heating;

1: 94 percent / pyridine, N,N-dimethylaminopyridine 2: 87 percent / sodium azide / 1 h / Heating 3: 67 percent / H2 / 5percent Pd/C / methanol / 2585.7 Torr 4: 68 percent / diborane / tetrahydrofuran; hexane / 2 h / Heating View Scheme

1: 70 percent / lithium aluminum hydride / diethyl ether / 5 h / Heating 2: 93 percent / magnesium oxide / H2O / 3 h / 0 °C 3: 60 percent / 90percent aq. trifluoroacetic acid / 0.08 h / Ambient temperature 4: 80 percent / pyridine / 1.) 0 deg C, 1 h, 2.) 8 deg C, 40 h 5: 100 percent / 4-methylbenzenesulfonic acid / diethyl ether / Ambient temperature 6: 62 percent / sodium hydride / tetrahydrofuran / Ambient temperature 7: 70 percent / acetic acid, water / tetrahydrofuran / 1 h / Ambient temperature 8: 100 percent / H2 / 10percent Pd/C / ethanol / 2585.7 Torr View Scheme

1: 67 percent / H2 / 5percent Pd/C / methanol / 2585.7 Torr 2: 68 percent / diborane / tetrahydrofuran; hexane / 2 h / Heating View Scheme

1: 87 percent / sodium azide / 1 h / Heating 2: 67 percent / H2 / 5percent Pd/C / methanol / 2585.7 Torr 3: 68 percent / diborane / tetrahydrofuran; hexane / 2 h / Heating View Scheme

1: 93 percent / magnesium oxide / H2O / 3 h / 0 °C 2: 60 percent / 90percent aq. trifluoroacetic acid / 0.08 h / Ambient temperature 3: 80 percent / pyridine / 1.) 0 deg C, 1 h, 2.) 8 deg C, 40 h 4: 100 percent / 4-methylbenzenesulfonic acid / diethyl ether / Ambient temperature 5: 62 percent / sodium hydride / tetrahydrofuran / Ambient temperature 6: 70 percent / acetic acid, water / tetrahydrofuran / 1 h / Ambient temperature 7: 100 percent / H2 / 10percent Pd/C / ethanol / 2585.7 Torr View Scheme

1: 80 percent / pyridine / 1.) 0 deg C, 1 h, 2.) 8 deg C, 40 h 2: 100 percent / 4-methylbenzenesulfonic acid / diethyl ether / Ambient temperature 3: 62 percent / sodium hydride / tetrahydrofuran / Ambient temperature 4: 70 percent / acetic acid, water / tetrahydrofuran / 1 h / Ambient temperature 5: 100 percent / H2 / 10percent Pd/C / ethanol / 2585.7 Torr View Scheme

1: 60 percent / 90percent aq. trifluoroacetic acid / 0.08 h / Ambient temperature 2: 80 percent / pyridine / 1.) 0 deg C, 1 h, 2.) 8 deg C, 40 h 3: 100 percent / 4-methylbenzenesulfonic acid / diethyl ether / Ambient temperature 4: 62 percent / sodium hydride / tetrahydrofuran / Ambient temperature 5: 70 percent / acetic acid, water / tetrahydrofuran / 1 h / Ambient temperature 6: 100 percent / H2 / 10percent Pd/C / ethanol / 2585.7 Torr View Scheme