trifluoroacetic acid T=0°C; 1 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 5: CF3COOH / 0.5 h / 0 °C 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 3: CF3COOH / 0.5 h / 0 °C 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 4: CF3COOH / 0.5 h / 0 °C 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 6: CF3COOH / 0.5 h / 0 °C View Scheme

1: 63.5 percent / 1.) Na/NH3 (liq.) / 1.) THF, temperature of liquid NH3, 2.) room temperature, 18.5 h 2: CF3COOH / 0.5 h / 0 °C View Scheme

1: 1) Na / 1) dioxane, reflux, 15 h; 2) THF, room temp. 2: 94 percent / trifluoroacetic acid / 1 h / 0 °C View Scheme

1: 1) Na / 1) dioxane, reflux, 15 h; 2) THF, room temp. 2: 94 percent / trifluoroacetic acid / 1 h / 0 °C View Scheme