1: 99 percent / diethyl ether / 0.25 h / 0 °C 2: 96 percent / hydroxylamine hydrochloride, KOH / methanol / 1.) 0 deg C, 5 min, 2.) 0 deg C, 30 min 3: 69 percent / NaIO4 / H2O / 0.17 h / 0 °C 4: 85 percent / Na2HPO4, 5percent sodium amalgam / ethanol / 1 h 5: 90 percent / imidazole / dimethylformamide / 1 h / Ambient temperature 6: 76 percent / N-methylmorpholine N-oxide monohydrate, 4percent aq. OsO4 / acetonitrile; H2O / 14 h / Ambient temperature 7: 99 percent / pyridinium p-toluenesulfonate / benzene / 13 h / 55 °C 8: 71 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating 9: CBr4, PPh3 / CH2Cl2 / 0.33 h / 0 °C 10: Et3N / CH2Cl2 / 0.5 h / 0 °C 11: 86 percent / H2 / PdCl2 / methanol / 0.5 h 12: 66 percent / 2 N aq. HCl / tetrahydrofuran / 14 h / Ambient temperature View Scheme