ammonia; sodium 1.) THF, temperature of liquid NH3, 2.) room temperature, 18.5 h;

1: 69.6 percent / Et3N / dioxane; H2O / 15 h / 50 °C 2: 81 percent / LiAlH4 / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 15 h 3: pyridine / 1.) 0 deg C, 2.) stored in the refrigerator for 5 days 4: 63.5 percent / 1.) Na/NH3 (liq.) / 1.) THF, temperature of liquid NH3, 2.) room temperature, 18.5 h View Scheme

1: 69.6 percent / Et3N / dioxane; H2O / 15 h / 50 °C 2: 81 percent / LiAlH4 / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 15 h 3: pyridine / 1.) 0 deg C, 2.) stored in the refrigerator for 5 days 4: 63.5 percent / 1.) Na/NH3 (liq.) / 1.) THF, temperature of liquid NH3, 2.) room temperature, 18.5 h View Scheme

1: pyridine / 1.) 0 deg C, 2.) stored in the refrigerator for 5 days 2: 63.5 percent / 1.) Na/NH3 (liq.) / 1.) THF, temperature of liquid NH3, 2.) room temperature, 18.5 h View Scheme

1: 81 percent / LiAlH4 / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 15 h 2: pyridine / 1.) 0 deg C, 2.) stored in the refrigerator for 5 days 3: 63.5 percent / 1.) Na/NH3 (liq.) / 1.) THF, temperature of liquid NH3, 2.) room temperature, 18.5 h View Scheme

1: 95 percent / HCl / 2 h / Heating 2: 69.6 percent / Et3N / dioxane; H2O / 15 h / 50 °C 3: 81 percent / LiAlH4 / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 15 h 4: pyridine / 1.) 0 deg C, 2.) stored in the refrigerator for 5 days 5: 63.5 percent / 1.) Na/NH3 (liq.) / 1.) THF, temperature of liquid NH3, 2.) room temperature, 18.5 h View Scheme

in tetrahydrofuran T=20°C; 35 h; Inert atmosphere;

sodium 1) dioxane, reflux, 15 h; 2) THF, room temp.; Yield given. Multistep reaction;

trifluoroacetic acid T=0°C; 1 h;