diborane in tetrahydrofuran 1 h; Heating; Yield given;

lithium aluminium tetrahydride; sulfuric acid 1) THF, 0 deg C, 0.5 h; 2) 1 h; Yield given. Multistep reaction;

1: 86 percent / acetic acid / 0.08 h / Heating 2: 64 percent / HCl (g) / diethyl ether / 10 degC, 3h, then r.t., overnight 3: 83 percent / H2O / 1 h / 80 °C 4: 87 percent / triethylamine / toluene / 6 h / 95 °C / r.t., overnight 5: H2 / PtO2 / ethyl acetate / 3.5 h / Ambient temperature 6: H2 / PtO2 / acetic acid; ethyl acetate / 1.5 h / Ambient temperature 7: 90 percent / triethylamine / tetrahydrofuran / Ambient temperature; overnight 8: 96 percent / H2 / 5percent Pd-on-carbon / acetic acid; ethanol / 1.5 h / 40 °C / 2280 Torr 9: 1M diborane / tetrahydrofuran / 1 h / Heating View Scheme

1: 64 percent / HCl (g) / diethyl ether / 10 degC, 3h, then r.t., overnight 2: 83 percent / H2O / 1 h / 80 °C 3: 87 percent / triethylamine / toluene / 6 h / 95 °C / r.t., overnight 4: H2 / PtO2 / ethyl acetate / 3.5 h / Ambient temperature 5: H2 / PtO2 / acetic acid; ethyl acetate / 1.5 h / Ambient temperature 6: 90 percent / triethylamine / tetrahydrofuran / Ambient temperature; overnight 7: 96 percent / H2 / 5percent Pd-on-carbon / acetic acid; ethanol / 1.5 h / 40 °C / 2280 Torr 8: 1M diborane / tetrahydrofuran / 1 h / Heating View Scheme

1: 12N hydrochloric acid / ethanol / Ambient temperature; overnight 2: 86 percent / acetic acid / 0.08 h / Heating 3: 64 percent / HCl (g) / diethyl ether / 10 degC, 3h, then r.t., overnight 4: 83 percent / H2O / 1 h / 80 °C 5: 87 percent / triethylamine / toluene / 6 h / 95 °C / r.t., overnight 6: H2 / PtO2 / ethyl acetate / 3.5 h / Ambient temperature 7: H2 / PtO2 / acetic acid; ethyl acetate / 1.5 h / Ambient temperature 8: 90 percent / triethylamine / tetrahydrofuran / Ambient temperature; overnight 9: 96 percent / H2 / 5percent Pd-on-carbon / acetic acid; ethanol / 1.5 h / 40 °C / 2280 Torr 10: 1M diborane / tetrahydrofuran / 1 h / Heating View Scheme

1: 1. Br2 / Ambient temperature; 1. CCl4, irradiation, reflux, 4h; 2. r.t., overnight 2: 12N hydrochloric acid / ethanol / Ambient temperature; overnight 3: 86 percent / acetic acid / 0.08 h / Heating 4: 64 percent / HCl (g) / diethyl ether / 10 degC, 3h, then r.t., overnight 5: 83 percent / H2O / 1 h / 80 °C 6: 87 percent / triethylamine / toluene / 6 h / 95 °C / r.t., overnight 7: H2 / PtO2 / ethyl acetate / 3.5 h / Ambient temperature 8: H2 / PtO2 / acetic acid; ethyl acetate / 1.5 h / Ambient temperature 9: 90 percent / triethylamine / tetrahydrofuran / Ambient temperature; overnight 10: 96 percent / H2 / 5percent Pd-on-carbon / acetic acid; ethanol / 1.5 h / 40 °C / 2280 Torr 11: 1M diborane / tetrahydrofuran / 1 h / Heating View Scheme

1: hydrazine hydrate / ethanol / 4 h / Heating 2: 86 percent / acetic acid / 0.08 h / Heating 3: 64 percent / HCl (g) / diethyl ether / 10 degC, 3h, then r.t., overnight 4: 83 percent / H2O / 1 h / 80 °C 5: 87 percent / triethylamine / toluene / 6 h / 95 °C / r.t., overnight 6: H2 / PtO2 / ethyl acetate / 3.5 h / Ambient temperature 7: H2 / PtO2 / acetic acid; ethyl acetate / 1.5 h / Ambient temperature 8: 90 percent / triethylamine / tetrahydrofuran / Ambient temperature; overnight 9: 96 percent / H2 / 5percent Pd-on-carbon / acetic acid; ethanol / 1.5 h / 40 °C / 2280 Torr 10: 1M diborane / tetrahydrofuran / 1 h / Heating View Scheme

1: 85 percent / dimethylformamide / 3 h / Heating 2: hydrazine hydrate / ethanol / 4 h / Heating 3: 86 percent / acetic acid / 0.08 h / Heating 4: 64 percent / HCl (g) / diethyl ether / 10 degC, 3h, then r.t., overnight 5: 83 percent / H2O / 1 h / 80 °C 6: 87 percent / triethylamine / toluene / 6 h / 95 °C / r.t., overnight 7: H2 / PtO2 / ethyl acetate / 3.5 h / Ambient temperature 8: H2 / PtO2 / acetic acid; ethyl acetate / 1.5 h / Ambient temperature 9: 90 percent / triethylamine / tetrahydrofuran / Ambient temperature; overnight 10: 96 percent / H2 / 5percent Pd-on-carbon / acetic acid; ethanol / 1.5 h / 40 °C / 2280 Torr 11: 1M diborane / tetrahydrofuran / 1 h / Heating View Scheme

1: 87 percent / triethylamine / toluene / 6 h / 95 °C / r.t., overnight 2: H2 / PtO2 / ethyl acetate / 3.5 h / Ambient temperature 3: H2 / PtO2 / acetic acid; ethyl acetate / 1.5 h / Ambient temperature 4: 90 percent / triethylamine / tetrahydrofuran / Ambient temperature; overnight 5: 96 percent / H2 / 5percent Pd-on-carbon / acetic acid; ethanol / 1.5 h / 40 °C / 2280 Torr 6: 1M diborane / tetrahydrofuran / 1 h / Heating View Scheme

1: 90 percent / triethylamine / tetrahydrofuran / Ambient temperature; overnight 2: 96 percent / H2 / 5percent Pd-on-carbon / acetic acid; ethanol / 1.5 h / 40 °C / 2280 Torr 3: 1M diborane / tetrahydrofuran / 1 h / Heating View Scheme