ammonia; hydrogen; nickel in methanol Catalytic hydrogenation;

1: 98 percent / NaH; NaI / dimethylformamide 2: 91 percent / H2; NH3 / Raney Ni / methanol View Scheme

1: 98 percent / NaH; NaI / dimethylformamide 2: 91 percent / H2; NH3 / Raney Ni / methanol View Scheme

1: 44 percent / DCC, DMAP / CH2Cl2 / 96 h / 0 deg C to r.t. 2: 2.46 g / TFA / CH2Cl2 / 1) 3 min, 0 deg C, 2) 17 min, without cooling 3: 78 percent / pyridine / 1.87 h / 101 °C 4: H2, 0.1N aq.HCl / 10percent Pd-C / methanol / 2.33 h View Scheme

1: 99 percent / diphenyl phosphorazidate, triethylamine / dimethylformamide / 17 h / 0 - 20 °C 2: 87 percent / trifluoroacetic acid (TFA) / CH2Cl2 / 0.75 h / 0 - 20 °C 3: 96 percent / pyridine 4: 95 percent / diphenyl phosphorazidate, triethylamine / dimethylformamide / 17 h / 0 - 20 °C 5: 100 percent / trifluoroacetic acid (TFA) / CH2Cl2 6: 91 percent / pyridine / 12 h 7: H2, HCl / 10percent Pd/C / methanol View Scheme

1: 44 percent / DCC, DMAP / CH2Cl2 / 96 h / 0 deg C to r.t. 2: 2.46 g / TFA / CH2Cl2 / 1) 3 min, 0 deg C, 2) 17 min, without cooling 3: 78 percent / pyridine / 1.87 h / 101 °C 4: 21 percent / H2, NH3, conc.NH4OH / Raney nickel W-2 / methanol / 3 h / 0 °C / 2947.7 - 3102.9 Torr 5: 54 percent / diphenylphosphoryl azide / dimethylformamide / 96 h / -1 - 8 °C 6: 100 percent / H2 / 10percent Pd-C / methanol / 7 h View Scheme