1: 87 percent / Li/NH3; t-BuOH; NH4SO4 / tetrahydrofuran / 0.17 h / -78 °C 2: pyridine / CH2Cl2 / -18 °C 3: 63 percent / NaN3 / dimethylformamide / 5 h / 20 °C 4: 94 percent / AcOH / H2O / 0.5 h / 80 °C 5: 77 percent / Ph3P / pyridine; H2O / 5 h / 60 °C 6: 73 percent / H2 / Pd/C / ethanol / 3 h / 760 Torr View Scheme

1: 87 percent / Li/NH3; t-BuOH; NH4SO4 / tetrahydrofuran / 0.17 h / -78 °C 2: pyridine / CH2Cl2 / -18 °C 3: 63 percent / NaN3 / dimethylformamide / 5 h / 20 °C 4: 94 percent / AcOH / H2O / 0.5 h / 80 °C 5: 77 percent / Ph3P / pyridine; H2O / 5 h / 60 °C 6: 73 percent / H2 / Pd/C / ethanol / 3 h / 760 Torr View Scheme

1: 87 percent / Li/NH3; t-BuOH; NH4SO4 / tetrahydrofuran / 0.17 h / -78 °C 2: pyridine / CH2Cl2 / -18 °C 3: 63 percent / NaN3 / dimethylformamide / 5 h / 20 °C 4: 94 percent / AcOH / H2O / 0.5 h / 80 °C 5: 77 percent / Ph3P / pyridine; H2O / 5 h / 60 °C 6: 69 percent / Red-Al / diethyl ether / 24 h / 0 °C View Scheme

1: 87 percent / Li/NH3; t-BuOH; NH4SO4 / tetrahydrofuran / 0.17 h / -78 °C 2: pyridine / CH2Cl2 / -18 °C 3: 63 percent / NaN3 / dimethylformamide / 5 h / 20 °C 4: 94 percent / AcOH / H2O / 0.5 h / 80 °C 5: 77 percent / Ph3P / pyridine; H2O / 5 h / 60 °C 6: 73 percent / H2 / Pd/C / ethanol / 3 h / 760 Torr View Scheme