sodium hydroxide; tetra(n-butyl)ammonium hydroxide in dichloromethane 72 h; Ambient temperature;

caesium carbonate

1: 61 percent / m-chloroperoxybenzoic acid, Na2HPO4 / CH2Cl2 2: 95 percent / water / Ambient temperature View Scheme

1: 98 percent / p-TsOH / CH2Cl2 / 1 h / -15 - -10 °C 2: 81 percent / m-chloroperbenzoic acid / CH2Cl2 / 8 h / 0 °C 3: 90 percent / <(i-PrO)3P>4Pd / tetrahydrofuran; dimethylsulfoxide; hexane / 1) 0 deg C, 3 h, 2) rt, 16 h 4: 64 percent / methanol; dimethylsulfoxide / 16 h / 90 °C 5: 90 percent / dimethylaminopyridine, Et2NSF3 / CH2Cl2 / 1) -78 deg C to rt, 2 h, 2) rt, 22 h 6: 30percent aq. NH4OH / methanol / 12 h 7: 10 percent aq. HCl / 3 h View Scheme

osmium(VIII) oxide; 4-methylmorpholine N-oxide in dichloromethane T=30°C; 24 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

osmium(VIII) oxide; 4-methylmorpholine N-oxide in dichloromethane T=4°C; 24 h;

oxygen; methylene blue in dichloromethane T=-80°C;

palladium on activated charcoal in methanol T=30°C; 0.166667 h; atmospheric pressure;

palladium on activated charcoal in methanol T=30°C; 0.166667 h; atmospheric pressure;

5 rhodium-on-charcoal; hydrogen in methanol T=25°C; P=2250.23 Torr; 0.05 h;