chloroform; hydrogen; palladium on activated charcoal in methanol P=1551.4 Torr; 1 h;

1: triethylamine / toluene / 0.08 h / 0 °C 2: NaN3 / tetrabutylammonium bromide / toluene; H2O / 3 h / 60 °C 3: 99 percent / H2, CHCl3 / Pd-C / methanol / 1 h / 1551.4 Torr View Scheme

1: 100 percent / CH2Cl2 / 12 h 2: triethylamine / toluene / 0.08 h / 0 °C 3: NaN3 / tetrabutylammonium bromide / toluene; H2O / 3 h / 60 °C 4: 99 percent / H2, CHCl3 / Pd-C / methanol / 1 h / 1551.4 Torr View Scheme

1: NaN3 / tetrabutylammonium bromide / toluene; H2O / 3 h / 60 °C 2: 99 percent / H2, CHCl3 / Pd-C / methanol / 1 h / 1551.4 Torr View Scheme