triethylamine in dichloromethane T=20°C; 2.5 h;

1.1: HNO2 1.2: copper(I) bromide; HBr 2.1: 85 percent / copper(I) iodide; potassium carbonate; (+/-)-trans-1,2-diaminocyclohexane / dioxane / 15 h / 110 °C 3.1: 80 percent / pyridinium p-toluenesulfonate / ethanol / 0.5 h / Heating 4.1: triethylamine / CH2Cl2 / 1 h / 0 - 25 °C View Scheme

1: 85 percent / copper(I) iodide; potassium carbonate; (+/-)-trans-1,2-diaminocyclohexane / dioxane / 15 h / 110 °C 2: 80 percent / pyridinium p-toluenesulfonate / ethanol / 0.5 h / Heating 3: triethylamine / CH2Cl2 / 1 h / 0 - 25 °C View Scheme

1: 80 percent / pyridinium p-toluenesulfonate / ethanol / 0.5 h / Heating 2: triethylamine / CH2Cl2 / 1 h / 0 - 25 °C View Scheme

1.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 42 h / 0 °C 2.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C 3.1: triethylamine / dichloromethane / 2.5 h / 20 °C View Scheme

1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C 2: triethylamine / dichloromethane / 2.5 h / 20 °C View Scheme

1.1: sodium azide / N,N-dimethyl-formamide / 3.5 h / 80 °C 2.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 12 h / 20 °C / 9000.9 Torr 3.1: (2R,3R)-(-)-di-O-(p-toluoyl)-tartaric acid / dimethyl sulfoxide / 3 h / 20 °C / Resolution of racemate 3.2: 1 h / 20 °C View Scheme

1: sodium azide / N,N-dimethyl-formamide / 3.5 h / 80 °C 2: palladium 10 on activated carbon; hydrogen / ethyl acetate / 12 h / 20 °C / 9000.9 Torr 3: pyridine / ethyl acetate / 1 h / 20 °C View Scheme