Multi-step reaction with 13 steps
1.1: ethanol / 3 h / Inert atmosphere; Reflux
2.1: toluene-4-sulfonic acid / 20 °C / Inert atmosphere
2.2: 0.33 h
3.1: hydrogen / palladium 10% on activated carbon / 1,4-dioxane; water / 18 h / 20 °C / 760.05 Torr
4.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
5.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere
5.2: 0 - 20 °C
6.1: manganese(IV) oxide / dichloromethane / 2 h / 20 °C
7.1: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C
7.2: pH ~ 8
8.1: triethylamine / chloroform / 4.5 h / Reflux; Inert atmosphere
9.1: pyridine / acetonitrile / 50 - 90 °C / Reflux; Inert atmosphere
10.1: hydrogenchloride / 1,4-dioxane; dichloromethane / 20 °C
11.1: ammonia / methanol; water
12.1: magnesium sulfate / methanol; dichloromethane / 2 h / 20 °C
13.1: sodium tris(acetoxy)borohydride / methanol; dichloromethane / 20 °C
With
pyridine; hydrogenchloride; manganese(IV) oxide; ammonia; water; hydrogen; sodium tris(acetoxy)borohydride; sodium hydride; magnesium sulfate; potassium carbonate; toluene-4-sulfonic acid; triethylamine;
palladium 10% on activated carbon;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;