2: 2 N HCl, H2 / 5percent rhodium/carbon / ethanol / 24 h / Ambient temperature 3: 4 N HCl / 1 h / 70 °C View Scheme

1: 77.5 percent / p-TsOH / tetrahydrofuran / 84 h / Ambient temperature 2: 88 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 3: 64 percent / p-TsOH / methanol / 20 h / 4 °C 4: 81 percent / triphenylphosphine, CCl4 / CH2Cl2 / a) 40 deg C, 16 h, b) 60 deg C, 7 h 5: 67 percent / lithium azide / dimethylformamide / 72 h / 60 °C 6: 82 percent / AcOH / H2O; tetrahydrofuran / a) room temp., 6 h, b) 60 deg C, 20 h 8: 2 N HCl, H2 / 5percent rhodium/carbon / ethanol / 24 h / Ambient temperature 9: 4 N HCl / 1 h / 70 °C View Scheme