1: 83 percent / NH3 / methanol / 192 h / 20 °C 2: 60.5 percent / LiAlH4 / diethyl ether / 48 h / Heating 3: 66 percent / Na / tetrahydrofuran; liquid ammonia / 1.5 h / -33 °C 4: 65 percent / BBr3 / CH2Cl2 / 20 °C View Scheme

1: 83 percent / NH3 / methanol / 192 h / 20 °C 2: 60.5 percent / LiAlH4 / diethyl ether / 48 h / Heating 3: 66 percent / Na / tetrahydrofuran; liquid ammonia / 1.5 h / -33 °C View Scheme

1: 90 percent / NaCN / methanol / 96 h / 50 °C 2: 90 percent / LiAlH4 / diethyl ether / 48 h / Heating 3: 80 percent / Na / tetrahydrofuran; liquid ammonia / 1.5 h / -33 °C 4: 23 percent / BBr3 / CH2Cl2 / 20 °C View Scheme

1: 83 percent / NH3 / methanol / 192 h / 20 °C 2: 60.5 percent / LiAlH4 / diethyl ether / 48 h / Heating 3: 66 percent / Na / tetrahydrofuran; liquid ammonia / 1.5 h / -33 °C 4: 83 percent / Et3N / CH2Cl2 / 0.25 h / 20 °C View Scheme

1: 90 percent / NaCN / methanol / 96 h / 50 °C 2: 90 percent / LiAlH4 / diethyl ether / 48 h / Heating 3: 80 percent / Na / tetrahydrofuran; liquid ammonia / 1.5 h / -33 °C View Scheme