Multi-step reaction with 10 steps
1.1: triethylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
2.1: sodium tetrahydroborate; ethanol / tetrahydrofuran / 0 - 20 °C
3.1: Dess-Martin periodane / 0 - 20 °C / Inert atmosphere
4.1: hydrogenchloride / dichloromethane; water; 1,4-dioxane / 1 h / 0 °C
4.2: 1.5 h / 0 °C
5.1: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 16 h / 115 °C / Inert atmosphere
6.1: hydrogen / ethanol; methanol / 16 h
7.1: sodium bis(2-methoxyethoxy)aluminium dihydride / dichloromethane / 5 h / 20 - 40 °C / Inert atmosphere
8.1: dichloromethane / 18 h / 0 - 23 °C
9.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C
9.2: 23 °C
9.3: 23 °C
10.1: hydroxylamine / ethanol / 18 h / 85 °C
With
hydrogenchloride; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium(0); ethanol; hydrogen; hydroxylamine; sodium hydride; caesium carbonate; Dess-Martin periodane; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;