Multi-step reaction with 12 steps
1.1: toluene / 18 h / 90 °C
1.2: 1 h / -78 - -60 °C
2.1: sodium hydrogencarbonate; ozone / methanol; dichloromethane; oxygen / 0.17 h / -78 °C
2.2: 0.67 h / -78 - 0 °C
2.3: Cooling with ice
3.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
4.1: sodium carbonate / dichloromethane; water / 1 h / Cooling with ice
5.1: potassium tert-butylate / tert-butyl alcohol / 3 h / Reflux
6.1: Lawessons reagent / tetrahydrofuran / 1 h / Reflux
7.1: ammonia / methanol / 6 h / 20 °C
8.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 4 h / 20 °C / Cooling with ice
9.1: sodium azide; sodium L-ascorbate / copper(l) iodide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane / ethanol; water / 70 °C / Inert atmosphere
10.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran; ethanol
11.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane
12.1: hydrogenchloride / 1,4-dioxane; methanol / 3.25 h / 50 °C
With
Lawessons reagent; hydrogenchloride; sodium azide; 1-hydroxy-7-aza-benzotriazole; potassium tert-butylate; ammonia; hydrogen; sodium hydrogencarbonate; sodium carbonate; ozone; sodium L-ascorbate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine;
copper(l) iodide; palladium 10% on activated carbon; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; oxygen; toluene; tert-butyl alcohol;