1: N-bromosuccinimide / CCl4 / Heating 2: 37 percent / N-methylmorpholine N-oxide, OsO4 / tetrahydrofuran; acetonitrile; 2-methyl-propan-2-ol / 48 h / Ambient temperature 3: 96 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / Ambient temperature 4: 89 percent / sodium methoxide / dimethylsulfoxide / 12 h / 50 °C 5: 89 percent / perchloric acid / acetone / 2 h / bath temperature 70 deg C View Scheme

1: N-bromosuccinimide / CCl4 / Heating 2: 50 percent / N-methylmorpholine N-oxide, OsO4 / tetrahydrofuran; acetonitrile; 2-methyl-propan-2-ol / 48 h / Ambient temperature 3: 97 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / Ambient temperature 4: 88 percent / sodium methoxide / dimethylsulfoxide / 12 h / 50 °C 5: 88 percent / perchloric acid / acetone / 2 h / bath temperature 70 deg C View Scheme