sodium tetrahydroborate in methanol

1: With sodium tetrahydroborate in methanol 1 h; 2: With hydrogenchloride in methanol; water T=20°C;

1: 32 percent / Et3N / CH2Cl2 / 2 h / 20 °C 2: 39 percent / SnCl2*2H2O; conc. HCl / ethanol / 20 °C 3: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C 4: 30 percent / NaBH4 / methanol / 1 h / 20 °C View Scheme

1: 32 percent / Et3N / CH2Cl2 / 2 h / 20 °C 2: 39 percent / SnCl2*2H2O; conc. HCl / ethanol / 20 °C 3: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C 4: 30 percent / NaBH4 / methanol / 1 h / 20 °C View Scheme

1: 39 percent / SnCl2*2H2O; conc. HCl / ethanol / 20 °C 2: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C 3: 30 percent / NaBH4 / methanol / 1 h / 20 °C View Scheme

1: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C 2: 30 percent / NaBH4 / methanol / 1 h / 20 °C View Scheme

1: 96 percent / hydroxylamine hydrochloride; sodium acetate / ethanol; H2O / 2 h / Heating 2: PCl5 / CH2Cl2 / 2 h / 20 °C 3: acetic acid; Zn / 0.5 h / Heating 4: BH3*THF / tetrahydrofuran / 0.5 h / Heating 5: 98 percent / triethylamine / CH2Cl2 / 1 h / 20 °C 6: 82 percent / hydrochloric acid; SnCl2 / ethanol / 2 h / Heating 7: triethylamine / CH2Cl2 / 1 h / 20 °C 8: NaOH / ethanol; H2O / 2 h / 50 °C View Scheme

1: 98 percent / triethylamine / CH2Cl2 / 1 h / 20 °C 2: 82 percent / hydrochloric acid; SnCl2 / ethanol / 2 h / Heating 3: triethylamine / CH2Cl2 / 1 h / 20 °C 4: NaOH / ethanol; H2O / 2 h / 50 °C View Scheme

1: PCl5 / CH2Cl2 / 2 h / 20 °C 2: acetic acid; Zn / 0.5 h / Heating 3: BH3*THF / tetrahydrofuran / 0.5 h / Heating 4: 98 percent / triethylamine / CH2Cl2 / 1 h / 20 °C 5: 82 percent / hydrochloric acid; SnCl2 / ethanol / 2 h / Heating 6: triethylamine / CH2Cl2 / 1 h / 20 °C 7: NaOH / ethanol; H2O / 2 h / 50 °C View Scheme

1: triethylamine / CH2Cl2 / 1 h / 20 °C 2: NaOH / ethanol; H2O / 2 h / 50 °C View Scheme