Multi-step reaction with 14 steps
1.1: aluminum (III) chloride / dichloromethane / 0.75 h / 0 °C
1.2: 15.5 h / 0 - 20 °C
1.3: Cooling
2.1: potassium carbonate / acetonitrile / 18 h / Reflux
3.1: hydroxylamine hydrochloride; sodium acetate / ethanol / 18 h / Reflux
4.1: hydrogen; ammonia / Raney nickel / ethanol; methanol / 20 h / 4395.87 Torr
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C
5.2: 0 °C
6.1: triethylamine / dichloromethane / 3 h / 20 °C
7.1: Chiralpak IA / ethyl acetate; hexane / Resolution of racemate
8.1: triethylamine / dichloromethane / 14 h / 0 - 20 °C
9.1: sodium azide / N,N-dimethyl-formamide / 2 h / 70 °C
10.1: hydrogen / palladium 10% on activated carbon / ethanol / 14 h / 20 °C / 3000.3 Torr / Inert atmosphere
11.1: ethanol / 5 h / 20 °C
11.2: 14 h / 0 - 20 °C
12.1: trifluoroacetic acid / dichloromethane
12.2: 1 h / Reflux
13.1: cesium fluoride; rac-diaminocyclohexane / copper(l) iodide / 1,4-dioxane / 95 °C / Inert atmosphere
14.1: 0.5 h / Reflux
14.2: 14 h / 20 °C
14.3: pH 7 / Buffer
With
aluminum (III) chloride; lithium aluminium tetrahydride; sodium azide; hydroxylamine hydrochloride; ammonia; hydrogen; sodium acetate; potassium carbonate; rac-diaminocyclohexane; triethylamine; cesium fluoride; trifluoroacetic acid;
copper(l) iodide; palladium 10% on activated carbon;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;