hydrogen; palladium on activated charcoal in ethanol

1: 249.3 g / p-toluenesulfonic acid / dimethylformamide; various solvent(s) / 2 h / 30 °C 2: 97 percent / triethylamine / acetone / 6 h / Ambient temperature 3: 70 percent / NaI, Zn / dimethylformamide / 3 h / 135 °C 4: 75 percent / N-methylmorpholine N-oxide hydrate, OsO4 / acetone; H2O; 2-methyl-propan-2-ol 5: 1.) dibutyltin oxide, 2.) tetrabutylammonium bromide / 1.) toluene, reflux 2.) toluene, 100 deg C, 8 h 6: 95 percent / pyridine / CH2Cl2 / 1 h 7: 10.6 g / lithium azide / CH2Cl2; dimethylformamide / 8 h / -40 °C 8: NiCl2, NaBH4 / ethanol / 0 °C 9: 9.6 g / pyridine / 2 h / 40 °C 10: 1.1 g / H2, glacial acetic acid / 10percent palladium-on-charcoal / methanol / 24 h / 2250.2 Torr 11: 100 percent / glacial acetic acid / H2O / 8 h / 60 °C View Scheme