bis(trifluoroacetoxy)borane-tetrahydrofuran in tetrahydrofuran; trifluoroacetic acid T=0 - 5°C; 0.0166667 h;

trifluorormethanesulfonic acid 3 h; Ambient temperature;

1: With sulfuric acid; trifluoroacetic acid in dichloromethane T=20°C; 2: With potassium carbonate; sodium chloride in water; ethyl acetate

hydrogen; acetic acid; palladium on activated charcoal T=50°C; 6 h;

1: 63 percent / dimethylformamide / 15 h / Heating 2: 70 percent / polyphosphoric acid / 2 h / 100 °C View Scheme

1: 63 percent / dimethylformamide / 15 h / Heating 2: 70 percent / polyphosphoric acid / 2 h / 100 °C View Scheme

1: 80.7 percent / Et3N / diethyl ether / 5 h / Ambient temperature 2: 68.4 percent / NaBH4 / methanol; H2O / 4 h / Ambient temperature 3: 87.3 percent / H2 / Raney-Ni / ethyl acetate / 16 h / 760 Torr / Ambient temperature 4: 88.8 percent / H2SO4 / CH2Cl2 / 0.5 h / 5 - 7 °C 5: 80.5 percent / glacial acetic acid / 4 h / Ambient temperature 6: H2, glacial acetic acid / 10percent Pd/C / 6 h / 50 °C View Scheme

1: NaBH4 / methanol / 2 h / 40 °C 2: 80.7 percent / Et3N / diethyl ether / 5 h / Ambient temperature 3: 68.4 percent / NaBH4 / methanol; H2O / 4 h / Ambient temperature 4: 87.3 percent / H2 / Raney-Ni / ethyl acetate / 16 h / 760 Torr / Ambient temperature 5: 88.8 percent / H2SO4 / CH2Cl2 / 0.5 h / 5 - 7 °C 6: 80.5 percent / glacial acetic acid / 4 h / Ambient temperature 7: H2, glacial acetic acid / 10percent Pd/C / 6 h / 50 °C View Scheme

1: 88.8 percent / H2SO4 / CH2Cl2 / 0.5 h / 5 - 7 °C 2: 80.5 percent / glacial acetic acid / 4 h / Ambient temperature 3: H2, glacial acetic acid / 10percent Pd/C / 6 h / 50 °C View Scheme

1: 68.4 percent / NaBH4 / methanol; H2O / 4 h / Ambient temperature 2: 87.3 percent / H2 / Raney-Ni / ethyl acetate / 16 h / 760 Torr / Ambient temperature 3: 88.8 percent / H2SO4 / CH2Cl2 / 0.5 h / 5 - 7 °C 4: 80.5 percent / glacial acetic acid / 4 h / Ambient temperature 5: H2, glacial acetic acid / 10percent Pd/C / 6 h / 50 °C View Scheme