Multi-step reaction with 9 steps
1.1: N-Bromosuccinimide / dichloromethane / 20 °C
2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C
2.2: 20 °C
3.1: sodium hydride / N,N-dimethyl-formamide / 1 h
3.2: 1.5 h / 60 °C
4.1: hydrogen / palladium 10% on activated carbon / methanol / 12 h
5.1: dmap / 1,4-dioxane / 6 h / Reflux
6.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 4 h / 20 °C
7.1: dichloromethane / 48 h / 20 °C
8.1: hydrogen / palladium 10% on activated carbon / methanol / 27 h
9.1: triethylamine / dichloromethane / 14 h / 0 - 20 °C
With
dmap; N-Bromosuccinimide; hydrogen; sodium tris(acetoxy)borohydride; sodium hydride; triethylamine;
palladium 10% on activated carbon;
In
1,4-dioxane; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; mineral oil;