sodium tetrahydroborate in ethanol T=0°C; 0.5 h;

1: CH2Cl2 / 1 h / 20 °C 2: NaOEt / ethanol / 3 h / Heating 3: 95 percent / NaBH4 / ethanol / 0.5 h / 0 °C View Scheme

1: NaOEt / ethanol / 3 h / Heating 2: 95 percent / NaBH4 / ethanol / 0.5 h / 0 °C View Scheme

1: CH2Cl2 / 1 h / 20 °C 2: NaOEt / ethanol / 3 h / Heating 3: 95 percent / NaBH4 / ethanol / 0.5 h / 0 °C View Scheme

1: LAH / tetrahydrofuran / -5 °C 2: NaHCO3 / dioxane; H2O View Scheme

1: LiAlH4 / tetrahydrofuran / 0.5 h / -5 °C 2: dioxane; H2O / 0.5 h 3: 85 percent / Et3N, pyridine-SO3, DMSO / 3 h / Ambient temperature 4: 88 percent / hydroxylamine hydrochloride, aq. NaHCO3 / ethanol; tetrahydrofuran / 1 h / 40 °C 5: 94 percent / AcCl, MeOH / 0.83 h / Ambient temperature 6: 85 percent / DBU / acetonitrile / 0.5 h / Ambient temperature View Scheme

lithium aluminium tetrahydride in tetrahydrofuran T=-5°C; 0.5 h;