2-chloro-1-methyl-pyridinium iodide; triethylamine in dichloromethane T=20°C; Mukaiyama reaction; 48 h; Inert atmosphere;

1: trans-(R)-4-(1-aminoethyl)cyclohexanecarboxylic acid With sodium hydroxide in tetrahydrofuran; water T=0°C; 0.5 h; 2: di-tert-butyl dicarbonate in tetrahydrofuran; water T=20°C; 48 h; 3: With hydrogenchloride in water 3 - 4 h;

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 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 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 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 View Scheme