pyridine; hydroxylamine hydrochloride in methanol 12 h; Ambient temperature;

1: 1.) O3, 2.) Me2S / 1.) AcOEt, -78 deg C, 15 min, 2.) -78 deg C, 20 min 2: 61 percent / H2NOH*HCl, pyridine / methanol / 12 h / Ambient temperature View Scheme

1: 2.) KOH, n-Bu4NBr, H2O / 2.) C6H6, room temperature, 24 h 2: 99 percent / MCPBA / CH2Cl2 / 0.33 h / -78 °C 3: 78 percent / toluene / 20 h / Heating 4: 1.) O3, 2.) Me2S / 1.) AcOEt, -78 deg C, 15 min, 2.) -78 deg C, 20 min 5: 61 percent / H2NOH*HCl, pyridine / methanol / 12 h / Ambient temperature View Scheme

1: 99 percent / MCPBA / CH2Cl2 / 0.33 h / -78 °C 2: 78 percent / toluene / 20 h / Heating 3: 1.) O3, 2.) Me2S / 1.) AcOEt, -78 deg C, 15 min, 2.) -78 deg C, 20 min 4: 61 percent / H2NOH*HCl, pyridine / methanol / 12 h / Ambient temperature View Scheme

1: 78 percent / toluene / 20 h / Heating 2: 1.) O3, 2.) Me2S / 1.) AcOEt, -78 deg C, 15 min, 2.) -78 deg C, 20 min 3: 61 percent / H2NOH*HCl, pyridine / methanol / 12 h / Ambient temperature View Scheme

hydrogen; rhodium on alumina in methanol P=4180 Torr; Ambient temperature;