in ethanol

1.) Et2O, 0 deg C, 2 h, 2.) heating; Yield given. Multistep reaction;

1: 75 percent / hydroxylamine hydrochloride, NaOAc / ethanol; H2O / 12 h / Heating 2: 87 percent / hydrogen, conc. HCl / 10percent Pd/C / ethanol / 4 h / 22 °C 3: 85.7 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 4: 98 percent / H2O / 16 h 5: 90 percent / 5percent aq. K2CO3 / methanol / 2 h / 55 °C 6: 62.3 percent / boron trifluoride etherate / CH2Cl2 / 24 h / 22 °C 7: 50 percent / 1 N methanolic HCl / 72 h / 25 °C 8: 80.5 percent / paraformaldehyde / H2O / 1 h / Heating 9: 64 percent / manganese dioxide / H2O / 18 h / Ambient temperature 10: 93 percent / K2CO3 / methanol; H2O / 2 h / Heating View Scheme

1: 75 percent / hydroxylamine hydrochloride, NaOAc / ethanol; H2O / 12 h / Heating 2: 87 percent / hydrogen, conc. HCl / 10percent Pd/C / ethanol / 4 h / 22 °C 3: 85.7 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 4: 98 percent / H2O / 16 h 5: 90 percent / 5percent aq. K2CO3 / methanol / 2 h / 55 °C 6: 62.3 percent / boron trifluoride etherate / CH2Cl2 / 24 h / 22 °C 7: 50 percent / 1 N methanolic HCl / 72 h / 25 °C 8: 80.5 percent / paraformaldehyde / H2O / 1 h / Heating 9: 64 percent / manganese dioxide / H2O / 18 h / Ambient temperature View Scheme