thionyl chloride; triethylamine in dichloromethane

ruthenium trichloride; periodic acid in tetrachloromethane; acetonitrile 2 h; Ambient temperature;

hydrogen; palladium dihydroxide in methanol 0.25 h;

ruthenium trichloride; periodic acid in tetrachloromethane; acetonitrile 2 h; Ambient temperature;

1: 98 percent / Et3N / CH2Cl2 / 0.33 h / 20 °C 2: 78 percent / NaN3, nBu4NBr / toluene; H2O / 85 - 90 °C 3: H2, MeOH-HCl / Pd/C / 24 h / 4654.3 Torr / Ambient temperature View Scheme

Multi-step reaction with 3 steps 1: 80 percent / CAN / H2O; acetonitrile / 0.5 h / 0 °C2: 80 percent / K2CO3 / dioxane; H2O / 0.17 h / Ambient temperature3: 1.) (CF3CO)2O, sym-collidine, 2.) K2CO3, NaBH4 / 1.) MeCN, 0 deg C, 5 min, 2.) H2O, 0 deg C to room temperature, 15 min