hydrogenchloride in diethyl ether 3 h; Ambient temperature;

sodium hydroxide in water; isopropyl alcohol 24 h; Ambient temperature;

1: 92 percent / CH2Cl2 / 12 h 2: triethylamine / toluene / 0.08 h / 0 °C 3: NaN3 / tetrabutylammonium bromide / toluene; H2O / 3 h / 60 °C 4: 96 percent / H2, CHCl3 / Pd-C / methanol / 1 h / 1551.4 Torr View Scheme

1: triethylamine / toluene / 0.08 h / 0 °C 2: NaN3 / tetrabutylammonium bromide / toluene; H2O / 3 h / 60 °C 3: 96 percent / H2, CHCl3 / Pd-C / methanol / 1 h / 1551.4 Torr View Scheme

1: NaN3 / tetrabutylammonium bromide / toluene; H2O / 3 h / 60 °C 2: 96 percent / H2, CHCl3 / Pd-C / methanol / 1 h / 1551.4 Torr View Scheme