osmium(VIII) oxide; water; 4-methylmorpholine N-oxide in acetone; tert-butyl alcohol T=20°C; 20 h;

1: 96 percent / MeONa; methanol / 2 h / 20 °C 2: 85 percent / pyridine / 24 h / 20 °C 3: 97 percent / pyridine / CH2Cl2 / 4.5 h / 20 °C 4: 97 percent / Bu4NF / tetrahydrofuran / 2 h / 50 °C 5: 45 percent / N-methyl-morpholine oxide; OsO4; H2O / acetone; 2-methyl-propan-2-ol / 20 h / 20 °C View Scheme

1: 85 percent / pyridine / 24 h / 20 °C 2: 97 percent / pyridine / CH2Cl2 / 4.5 h / 20 °C 3: 97 percent / Bu4NF / tetrahydrofuran / 2 h / 50 °C 4: 45 percent / N-methyl-morpholine oxide; OsO4; H2O / acetone; 2-methyl-propan-2-ol / 20 h / 20 °C View Scheme

1: 97 percent / pyridine / CH2Cl2 / 4.5 h / 20 °C 2: 97 percent / Bu4NF / tetrahydrofuran / 2 h / 50 °C 3: 45 percent / N-methyl-morpholine oxide; OsO4; H2O / acetone; 2-methyl-propan-2-ol / 20 h / 20 °C View Scheme

1: 97 percent / Bu4NF / tetrahydrofuran / 2 h / 50 °C 2: 45 percent / N-methyl-morpholine oxide; OsO4; H2O / acetone; 2-methyl-propan-2-ol / 20 h / 20 °C View Scheme

1: 94 percent / NaH / acetonitrile / 0.33 h / 20 °C 2: 96 percent / MeONa; methanol / 2 h / 20 °C 3: 85 percent / pyridine / 24 h / 20 °C 4: 97 percent / pyridine / CH2Cl2 / 4.5 h / 20 °C 5: 97 percent / Bu4NF / tetrahydrofuran / 2 h / 50 °C 6: 45 percent / N-methyl-morpholine oxide; OsO4; H2O / acetone; 2-methyl-propan-2-ol / 20 h / 20 °C View Scheme

1: 61 percent / copper; N-methylpyrrolidinone / 240 °C 2: 94 percent / NaH / acetonitrile / 0.33 h / 20 °C 3: 96 percent / MeONa; methanol / 2 h / 20 °C 4: 85 percent / pyridine / 24 h / 20 °C 5: 97 percent / pyridine / CH2Cl2 / 4.5 h / 20 °C 6: 97 percent / Bu4NF / tetrahydrofuran / 2 h / 50 °C 7: 45 percent / N-methyl-morpholine oxide; OsO4; H2O / acetone; 2-methyl-propan-2-ol / 20 h / 20 °C View Scheme

1.1: MeONa / 14 h / -20 - 4 °C 1.2: 80 percent / xylene / Heating 2.1: 99 percent / aq. NaOH / 2.5 h / Heating 3.1: 61 percent / copper; N-methylpyrrolidinone / 240 °C 4.1: 94 percent / NaH / acetonitrile / 0.33 h / 20 °C 5.1: 96 percent / MeONa; methanol / 2 h / 20 °C 6.1: 85 percent / pyridine / 24 h / 20 °C 7.1: 97 percent / pyridine / CH2Cl2 / 4.5 h / 20 °C 8.1: 97 percent / Bu4NF / tetrahydrofuran / 2 h / 50 °C 9.1: 45 percent / N-methyl-morpholine oxide; OsO4; H2O / acetone; 2-methyl-propan-2-ol / 20 h / 20 °C View Scheme

1: 99 percent / aq. NaOH / 2.5 h / Heating 2: 61 percent / copper; N-methylpyrrolidinone / 240 °C 3: 94 percent / NaH / acetonitrile / 0.33 h / 20 °C 4: 96 percent / MeONa; methanol / 2 h / 20 °C 5: 85 percent / pyridine / 24 h / 20 °C 6: 97 percent / pyridine / CH2Cl2 / 4.5 h / 20 °C 7: 97 percent / Bu4NF / tetrahydrofuran / 2 h / 50 °C 8: 45 percent / N-methyl-morpholine oxide; OsO4; H2O / acetone; 2-methyl-propan-2-ol / 20 h / 20 °C View Scheme