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: methanol / 2.5 h / 20 °C / Inert atmosphere
4.2: 0 - 50 °C
5.1: sodium tetrahydroborate; methanol / 0 - 20 °C / Inert atmosphere
6.1: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 16 h / 115 °C / Inert atmosphere
7.1: hydrogen / ethanol; methanol / 16 h
8.1: sodium bis(2-methoxyethoxy)aluminium dihydride / dichloromethane / 5 h / 20 - 40 °C / Inert atmosphere
9.1: dichloromethane / 18 h / 0 - 23 °C
10.1: N,N-dimethyl-formamide / 18 h / 23 °C
10.2: 0.5 h
With
methanol; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium(0); ethanol; hydrogen; caesium carbonate; Dess-Martin periodane; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;