methanol; sodium tetrahydroborate in dichloromethane T=20°C; 2.5 h;

1: methanol; sodium tetrahydroborate / dichloromethane / 2.5 h / 20 °C 2: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 12 h / 20 °C View Scheme

pyridine; 4-(N,N-dimethlyamino)pyridine; sodium tetrahydroborate Yield given. Multistep reaction;

palladium 10 on activated carbon; hydrogen; triethylamine in methanol T=55°C; 7 h;

1: 61 percent / K2CO3 / dimethylformamide / 16 h / 40 °C 2: 98 percent / HCO2NH4 / Pd-C / methanol / 2 h / Heating 3: 78 percent / Na, EtOH / 1 h / Ambient temperature View Scheme

1: 61 percent / K2CO3 / dimethylformamide / 16 h / 40 °C 2: 98 percent / HCO2NH4 / Pd-C / methanol / 2 h / Heating 3: 78 percent / Na, EtOH / 1 h / Ambient temperature View Scheme

1: trichlorophosphate / N,N-dimethyl-formamide / 6 h / 0 °C / Reflux 2: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 12 h / 70 °C / Inert atmosphere 3: potassium carbonate / dimethyl sulfoxide / 4 h / 40 - 50 °C 4: palladium 10 on activated carbon; hydrogen; triethylamine / methanol / 7 h / 55 °C View Scheme

1: potassium carbonate / dimethyl sulfoxide / 4 h / 40 - 50 °C 2: palladium 10 on activated carbon; hydrogen; triethylamine / methanol / 7 h / 55 °C View Scheme