osmium(VIII) oxide; trimethylamine-N-oxide in tert-butyl alcohol T=40°C; 24 h;

1: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C 2: 76 percent / PS-30 catalyst / various solvent(s) / 48 h 3: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h 4: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature 5: 99 percent / TEMPO, KBr, NaHCO3, NaOCl / CH2Cl2; H2O / 0.5 h 6: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C 7: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °C View Scheme

1: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C 2: 76 percent / PS-30 catalyst / various solvent(s) / 48 h 3: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h 4: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature View Scheme

1: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C 2: 76 percent / PS-30 catalyst / various solvent(s) / 48 h 3: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h 4: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature 5: 99 percent / TEMPO, KBr, NaHCO3, NaOCl / CH2Cl2; H2O / 0.5 h 6: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C 7: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °C 8: 93.4 percent / trifluoroacetic acid; toluene / 2 h / 110 °C 9: p-TSA*H2O / toluene; acetic acid / 18 h / 95 - 100 °C View Scheme

1: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C 2: 76 percent / PS-30 catalyst / various solvent(s) / 48 h 3: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h 4: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature 5: 99 percent / TEMPO, KBr, NaHCO3, NaOCl / CH2Cl2; H2O / 0.5 h 6: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C 7: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °C 8: 93.4 percent / trifluoroacetic acid; toluene / 2 h / 110 °C 9: p-TSA*H2O / toluene; acetic acid / 18 h / 95 - 100 °C 10: pyridine / 2 h / 20 - 25 °C View Scheme

1: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C 2: 76 percent / PS-30 catalyst / various solvent(s) / 48 h 3: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h 4: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature 5: 99 percent / TEMPO, KBr, NaHCO3, NaOCl / CH2Cl2; H2O / 0.5 h 6: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C 7: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °C 8: 93.4 percent / trifluoroacetic acid; toluene / 2 h / 110 °C 9: p-TSA*H2O / toluene; acetic acid / 18 h / 95 - 100 °C View Scheme

1: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C 2: 76 percent / PS-30 catalyst / various solvent(s) / 48 h 3: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h 4: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature 5: 99 percent / TEMPO, KBr, NaHCO3, NaOCl / CH2Cl2; H2O / 0.5 h 6: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C 7: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °C 8: 93.4 percent / trifluoroacetic acid; toluene / 2 h / 110 °C View Scheme