1: 80 percent / OsO4, N-methylmorpholine-N-oxide / H2O; acetone / 15 h 2: pyridine / 24 h / Ambient temperature 3: 0.50 g / NaOCH3 / methanol / 0.5 h / 50 - 60 °C View Scheme

Yield given. Multistep reaction;

1.1: K2OsO4*2H2O; potassium carbonate; potassium hexacyanoferrate(III) / tert-butyl alcohol; water / 17.5 h / 0 °C 2.1: pyridinium p-toluenesulfonate; orthoacetic acid trimethyl ester / dichloromethane / 0.33 h / 20 °C 2.2: 0.5 h / 20 °C 2.3: 1.5 h / 20 °C 3.1: water / 1.5 h / |Reflux View Scheme

osmium(VIII) oxide; 4-methylmorpholine N-oxide in water; acetone 15 h;

1.1: K2OsO4*2H2O; potassium carbonate; potassium hexacyanoferrate(III) / tert-butyl alcohol; water / 17.5 h / 0 °C 2.1: pyridinium p-toluenesulfonate; orthoacetic acid trimethyl ester / dichloromethane / 0.33 h / 20 °C 2.2: 0.5 h / 20 °C 2.3: 1.5 h / 20 °C View Scheme