Multi-step reaction with 12 steps
1.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 2.5 h / -65 °C
1.2: -80 - -40 °C
2.1: toluene / 4 h / 105 °C / Industry scale
3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 2 h / 25 °C
4.1: zinc; acetic acid / 2 h / 20 - 40 °C
5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 1.5 h / 80 °C
6.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 4 h
7.1: N-ethyl-N,N-diisopropylamine / acetonitrile
8.1: Lawessons reagent / tetrahydrofuran
9.1: ammonia / methanol / 15 h / 20 °C
10.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 4 h / 20 °C / Cooling with ice
11.1: sodium azide / copper(l) iodide; sodium L-ascorbate; (±)-N,N-dimethyl-trans-1,2-diaminocyclohexane / ethanol; water / 0.5 h / 70 °C / Inert atmosphere
12.1: hydrogen / palladium 10% on activated carbon / ethanol
With
Lawessons reagent; hydrogenchloride; n-butyllithium; sodium azide; ammonia; hydrogen; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropylamine; N-ethyl-N,N-diisopropylamine; zinc;
copper(l) iodide; palladium 10% on activated carbon; (±)-N,N-dimethyl-trans-1,2-diaminocyclohexane; sodium L-ascorbate;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; water; toluene; acetonitrile;