hydrogen; palladium on activated charcoal in ethanol P=2327.2 Torr; 2 h; Ambient temperature;

1: 1) NaH / 1) CH3CN, r.t., 1 h, 2) THF, r.t., 12 h 2: 87 percent / TFA / H2O / 0.5 h / Ambient temperature 3: 42 percent / H2 / 10percent Pd/C / ethanol / 2 h / 2327.2 Torr / Ambient temperature View Scheme

1: CCl4, hexamethylphosphorus triamide / 1) -78 to -40 deg C, 2) -40 deg C, 1 h, 3) to r.t., 1 h 2: 1) NaH / 1) CH3CN, r.t., 1 h, 2) THF, r.t., 12 h 3: 87 percent / TFA / H2O / 0.5 h / Ambient temperature 4: 42 percent / H2 / 10percent Pd/C / ethanol / 2 h / 2327.2 Torr / Ambient temperature View Scheme

1: 1) TFA, 2) NaN3 / 1) r.t., 1 h, 2) DMF, 110 deg C, 2 h 2: 1) NaH / 1) CH3CN, r.t., 1 h, 2) THF, r.t., 12 h 3: 87 percent / TFA / H2O / 0.5 h / Ambient temperature 4: 42 percent / H2 / 10percent Pd/C / ethanol / 2 h / 2327.2 Torr / Ambient temperature View Scheme

1: 1) NaH / 1) CH3CN, r.t., 1 h, 2) THF, r.t., 12 h 2: 87 percent / TFA / H2O / 0.5 h / Ambient temperature 3: 42 percent / H2 / 10percent Pd/C / ethanol / 2 h / 2327.2 Torr / Ambient temperature View Scheme

1: 87 percent / TFA / H2O / 0.5 h / Ambient temperature 2: 42 percent / H2 / 10percent Pd/C / ethanol / 2 h / 2327.2 Torr / Ambient temperature View Scheme