hydrogen; palladium on activated charcoal in methanol P=0.0006 Torr; 15 h; Ambient temperature;

pyridine; ammonium hydroxide; triphenylphosphine in 1,4-dioxane; water 24 h;

1: 93 percent / DMAP / CH2Cl2 / -50 deg C, 15 min; RT, 45 min 2: 90 percent / LiN3 / dimethylformamide / 2 h / Ambient temperature 3: 82 percent / Bu3SnH, AIBN / toluene / 1.5 h / Heating; via Staudinger reduction, too View Scheme

1: 90 percent / LiN3 / dimethylformamide / 2 h / Ambient temperature 2: 82 percent / Bu3SnH, AIBN / toluene / 1.5 h / Heating; via Staudinger reduction, too View Scheme