ammonia in tetrahydrofuran T=-78 - 24°C; P=6205.8 Torr; 60 h; Yield given;

triethylamine in dichloromethane T=-30°C; 0.5 h;

1: 70 percent / CuBr, NaOMe / 24 h / 70 °C 2: NaOH / methanol; H2O / 3 h / Ambient temperature 3: ethyl acetate / 6 h / 65 °C 4: 89 percent / NaBH4, BF3*Et2O / tetrahydrofuran / 16 h / 25 °C 5: Et3N / CH2Cl2 / 0.5 h / below 0 deg C View Scheme

1: 89 percent / NaBH4, BF3*Et2O / tetrahydrofuran / 16 h / 25 °C 2: Et3N / CH2Cl2 / 0.5 h / below 0 deg C View Scheme

1: ethyl acetate / 6 h / 65 °C 2: 89 percent / NaBH4, BF3*Et2O / tetrahydrofuran / 16 h / 25 °C 3: Et3N / CH2Cl2 / 0.5 h / below 0 deg C View Scheme

1: NaOH / methanol; H2O / 3 h / Ambient temperature 2: ethyl acetate / 6 h / 65 °C 3: 89 percent / NaBH4, BF3*Et2O / tetrahydrofuran / 16 h / 25 °C 4: Et3N / CH2Cl2 / 0.5 h / below 0 deg C View Scheme