hydrogen; palladium on activated charcoal in ethanol P=775.7 Torr; 1 h; Ambient temperature;

1: 76 percent / trifluoroacetic acid / 0.5 h / Ambient temperature 2: 74 percent / 1.) LiAlH4; 2.) HCl / tetrahydrofuran / 0.25 h / Heating 3: 34 percent / H2O / 1 h / Heating 4: 51 percent / H2 / 10percent Pd/C / ethanol / 1 h / 775.7 Torr / Ambient temperature View Scheme

1: 1.) pyrrolidine; 2.) 85percent N2H4 / 2.) Raney Ni / 1.) DMF, 125 deg C, 3 h; 2.) methanol, 50-60 deg C, 3 h 2: 76 percent / trifluoroacetic acid / 0.5 h / Ambient temperature 3: 74 percent / 1.) LiAlH4; 2.) HCl / tetrahydrofuran / 0.25 h / Heating 4: 34 percent / H2O / 1 h / Heating 5: 51 percent / H2 / 10percent Pd/C / ethanol / 1 h / 775.7 Torr / Ambient temperature View Scheme

1: 74 percent / 1.) LiAlH4; 2.) HCl / tetrahydrofuran / 0.25 h / Heating 2: 34 percent / H2O / 1 h / Heating 3: 51 percent / H2 / 10percent Pd/C / ethanol / 1 h / 775.7 Torr / Ambient temperature View Scheme

1: 34 percent / H2O / 1 h / Heating 2: 51 percent / H2 / 10percent Pd/C / ethanol / 1 h / 775.7 Torr / Ambient temperature View Scheme