Multi-step reaction with 10 steps
1.1: triethylamine / 1,2-dichloro-ethane / 4 h / 23 °C
2.1: Dess-Martin periodane / 0 - 20 °C / Inert atmosphere
3.1: hydrogenchloride / dichloromethane; water; 1,4-dioxane / 1 h / 0 °C
3.2: 1.5 h / 0 °C
4.1: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 16 h / 115 °C / Inert atmosphere
5.1: hydrogen / ethanol; methanol / 16 h
6.1: sodium bis(2-methoxyethoxy)aluminium dihydride / dichloromethane / 5 h / 20 - 40 °C / Inert atmosphere
7.1: dichloromethane / 18 h / 0 - 23 °C
8.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C
8.2: 23 °C
8.3: 23 °C
9.1: hydroxylamine / ethanol / 18 h / 85 °C
10.1: tetra-(n-butyl)ammonium iodide; boron trichloride / dichloromethane / 22 h / -50 - 23 °C / Inert atmosphere
With
hydrogenchloride; tris-(dibenzylideneacetone)dipalladium(0); hydrogen; hydroxylamine; boron trichloride; tetra-(n-butyl)ammonium iodide; sodium hydride; caesium carbonate; Dess-Martin periodane; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride;
In
1,4-dioxane; methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;