hydrogen; palladium on activated charcoal in methanol

palladium 10 on activated carbon; hydrogen P=760.051 Torr; 23 h;

sulfuric acid in diethylene glycol dimethyl ether

1: 23 h / 23 °C 2: palladium 10 on activated carbon; hydrogen / 23 h / 760.05 Torr View Scheme

triethylamine T=20°C; 0.166667 h;

sodium tetrahydroborate; magnesium sulfate; triethylamine 1.) MeOH, room temperature, 1.5 h, 2.) MeOH, -5 deg C (1.5 h), 0 deg C (1 h); Yield given. Multistep reaction;

1: 1.) Et3N, MgSO4, 2.) NaBH4 / 1.) MeOH, room temperature, 1.5 h, 2.) MeOH, -5 deg C (1.5 h), 0 deg C (1 h) 2: 91.1 percent / diisopropylethylamine / dimethylformamide / 1.) 0 deg C, 30 min, 2.) room temperature, 3 h 3: 89.2 percent / H2 / Pd/C / methanol / 4 h / 3102.9 Torr 4: 76.9 percent / aq. Et3N / acetonitrile / 4 h / Ambient temperature View Scheme