1.1: NaN3 / dimethylformamide / 12 h / 50 °C 2.1: NaOAc / methanol / 12 h 3.1: Et3N; DMAP / ethyl acetate / 4 h / 20 °C 3.2: 92 percent / H2 / Pd/C / ethyl acetate; methanol / 48 h View Scheme

1: NaN3 / dimethylformamide / 50 °C 2: H2 / 10percent Pd/C / methanol / 48 h / 760 Torr / Ambient temperature 3: 10percent aq. HCl / 2 h / Heating 4: aq. NaOH / 3 h / Ambient temperature View Scheme

1: NaN3 / dimethylformamide / 50 °C 2: H2 / 10percent Pd/C / methanol / 48 h / 760 Torr / Ambient temperature 3: 10percent aq. HCl / 2 h / Heating View Scheme

1: 78 percent / sodium azide / dimethylformamide / 2.5 h / 40 °C 2: 87 percent / K2CO3 / methanol / 0.33 h / 0 °C 3: 91 percent / H2 / Pd/C / ethyl acetate / 3.5 h / 760 Torr / Ambient temperature 4: 79 percent / pyridinium p-toluenesulfonate / benzene / 90 °C 5: LiOH / methanol; H2O / 1 h / Ambient temperature View Scheme

1: 78 percent / sodium azide / dimethylformamide / 2.5 h / 40 °C 2: 87 percent / K2CO3 / methanol / 0.33 h / 0 °C 3: 91 percent / H2 / Pd/C / ethyl acetate / 3.5 h / 760 Torr / Ambient temperature View Scheme

hydrogen; palladium on activated charcoal in methanol T=20°C; P=760 Torr; 48 h;