1: AcBr / CH2Cl2 / 2 h / -15 °C 2: NaN3 / dimethylformamide / 50 °C 3: H2 / 10percent Pd/C / methanol / 48 h / 760 Torr / Ambient temperature 4: 10percent aq. HCl / 2 h / Heating 5: aq. NaOH / 3 h / Ambient temperature View Scheme

1: AcBr / CH2Cl2 / 2 h / -15 °C 2: NaN3 / dimethylformamide / 50 °C 3: H2 / 10percent Pd/C / methanol / 48 h / 760 Torr / Ambient temperature 4: 10percent aq. HCl / 2 h / Heating View Scheme

1: 94 percent / ZnBr2 / CH2Cl2 / -15 deg C, 1 h then 0 deg C, 2 h 2: 78 percent / sodium azide / dimethylformamide / 2.5 h / 40 °C 3: 87 percent / K2CO3 / methanol / 0.33 h / 0 °C 4: 91 percent / H2 / Pd/C / ethyl acetate / 3.5 h / 760 Torr / Ambient temperature 5: 79 percent / pyridinium p-toluenesulfonate / benzene / 90 °C 6: LiOH / methanol; H2O / 1 h / Ambient temperature View Scheme

1: 94 percent / ZnBr2 / CH2Cl2 / -15 deg C, 1 h then 0 deg C, 2 h 2: 78 percent / sodium azide / dimethylformamide / 2.5 h / 40 °C 3: 87 percent / K2CO3 / methanol / 0.33 h / 0 °C 4: 91 percent / H2 / Pd/C / ethyl acetate / 3.5 h / 760 Torr / Ambient temperature View Scheme