hydrogenchloride; hydrogen; palladium 10 on activated carbon in tetrahydrofuran; methanol; water T=40°C; P=1838.93 - 2206.72 Torr; 4.5 h;

water; trifluoroacetic acid in dichloromethane T=20°C; 48 h;

hydrogen; palladium hydroxide - carbon in ethanol

palladium 10 on activated carbon; hydrogen in methanol; water T=20°C; 24 h;

hydrogenchloride T=80°C; 3 h;

1: 75 percent / Me3NO, OsO4 / 2-methyl-propan-2-ol; pyridine; H2O / 12 h / Heating 2: 90 percent / DMAP / triethylamine / 3 h / Heating 3: 90 percent / TFA, H2O / CH2Cl2 / 24 h / Ambient temperature 4: 93 percent / pyridine / CH2Cl2 / 1 h / 0 °C 5: 60 percent / NaN3, benzo-15-crown-5 / dimethylformamide / Ambient temperature 6: 90 percent / pyridine / CH2Cl2 / 0.17 h / 0 °C 7: 80 percent / tetrahydrofuran / 1 h / Ambient temperature 8: 91 percent / K2CO3 / methanol / 2 h / Ambient temperature 9: 80 percent / H2 / 20percent Pd(OH)2 on charcoal / ethanol View Scheme

1: 90 percent / DMAP / triethylamine / 3 h / Heating 2: 90 percent / TFA, H2O / CH2Cl2 / 24 h / Ambient temperature 3: 93 percent / pyridine / CH2Cl2 / 1 h / 0 °C 4: 60 percent / NaN3, benzo-15-crown-5 / dimethylformamide / Ambient temperature 5: 90 percent / pyridine / CH2Cl2 / 0.17 h / 0 °C 6: 80 percent / tetrahydrofuran / 1 h / Ambient temperature 7: 91 percent / K2CO3 / methanol / 2 h / Ambient temperature 8: 80 percent / H2 / 20percent Pd(OH)2 on charcoal / ethanol View Scheme

1: 90 percent / TFA, H2O / CH2Cl2 / 24 h / Ambient temperature 2: 93 percent / pyridine / CH2Cl2 / 1 h / 0 °C 3: 60 percent / NaN3, benzo-15-crown-5 / dimethylformamide / Ambient temperature 4: 90 percent / pyridine / CH2Cl2 / 0.17 h / 0 °C 5: 80 percent / tetrahydrofuran / 1 h / Ambient temperature 6: 91 percent / K2CO3 / methanol / 2 h / Ambient temperature 7: 80 percent / H2 / 20percent Pd(OH)2 on charcoal / ethanol View Scheme

1: 93 percent / pyridine / CH2Cl2 / 1 h / 0 °C 2: 60 percent / NaN3, benzo-15-crown-5 / dimethylformamide / Ambient temperature 3: 90 percent / pyridine / CH2Cl2 / 0.17 h / 0 °C 4: 80 percent / tetrahydrofuran / 1 h / Ambient temperature 5: 91 percent / K2CO3 / methanol / 2 h / Ambient temperature 6: 80 percent / H2 / 20percent Pd(OH)2 on charcoal / ethanol View Scheme

formic acid; palladium in methanol 20 h; Ambient temperature;