O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine in N,N-dimethyl-formamide T=20°C;

1.1: sodium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C 1.2: 48 h / 20 °C 1.3: 3 - 4 h 2.1: 2-chloro-1-methyl-pyridinium iodide; triethylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere View Scheme

1.1: chloroform / 0 °C 2.1: AlCl3, aluminium chloride / 1,2-dichloro-ethane / 4 h / 20 - 60 °C 3.1: sodium hypochlorite; sodium hydroxide / methanol; water / 2 h / 20 - 60 °C 4.1: ruthenium on carbon; ammonia; hydrogen / water / 144 h / 90 - 150 °C / 52505.3 Torr 5.1: sodium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C 5.2: 48 h / 20 °C 5.3: 3 - 4 h 6.1: 2-chloro-1-methyl-pyridinium iodide; triethylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere View Scheme

1.1: AlCl3, aluminium chloride / 1,2-dichloro-ethane / 4 h / 20 - 60 °C 2.1: sodium hypochlorite; sodium hydroxide / methanol; water / 2 h / 20 - 60 °C 3.1: ruthenium on carbon; ammonia; hydrogen / water / 144 h / 90 - 150 °C / 52505.3 Torr 4.1: sodium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C 4.2: 48 h / 20 °C 4.3: 3 - 4 h 5.1: 2-chloro-1-methyl-pyridinium iodide; triethylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere View Scheme

1.1: sodium hypochlorite; sodium hydroxide / methanol; water / 2 h / 20 - 60 °C 2.1: ruthenium on carbon; ammonia; hydrogen / water / 144 h / 90 - 150 °C / 52505.3 Torr 3.1: sodium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C 3.2: 48 h / 20 °C 3.3: 3 - 4 h 4.1: 2-chloro-1-methyl-pyridinium iodide; triethylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere View Scheme

1.1: ruthenium on carbon; ammonia; hydrogen / water / 144 h / 90 - 150 °C / 52505.3 Torr 2.1: sodium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C 2.2: 48 h / 20 °C 2.3: 3 - 4 h 3.1: 2-chloro-1-methyl-pyridinium iodide; triethylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere View Scheme