1: 88 percent / NaN3 / dimethylformamide / 32 h / 100 °C 2: 100 percent / LiAlH4 / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) reflux, 6 h 3: 88 percent / Na, NH3 / tetrahydrofuran / 0.5 h / -78 °C View Scheme

1: 88 percent / NaN3 / dimethylformamide / 32 h / 100 °C 2: 100 percent / LiAlH4 / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) reflux, 6 h 3: 88 percent / Na, NH3 / tetrahydrofuran / 0.5 h / -78 °C 4: 73 percent / Et3N, DMAP / tetrahydrofuran / 12 h View Scheme

1: 88 percent / NaN3 / dimethylformamide / 32 h / 100 °C 2: 100 percent / LiAlH4 / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) reflux, 6 h 3: 88 percent / Na, NH3 / tetrahydrofuran / 0.5 h / -78 °C 4: 73 percent / Et3N, DMAP / tetrahydrofuran / 12 h View Scheme