Multi-step reaction with 10 steps
1: sodium hydrogencarbonate / ethyl acetate; water / 2.5 h / 20 °C
2: potassium carbonate / toluene; acetone / 8 h / Reflux
3: toluene / 3 h / 85 °C / Inert atmosphere
4: sodium hydroxide; water; N-benzyl-N,N,N-triethylammonium chloride; Bromoform / 2 h / 60 °C
5: zinc; ammonium chloride / ethanol / 6 h / Reflux; Inert atmosphere
6: sulfuric acid / methanol / 60 h / Reflux; Inert atmosphere
7: dichloromethane; pyridine / 1 h / 20 °C
8: tri tert-butylphosphoniumtetrafluoroborate / tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane; dimethyl sulfoxide / 1.5 h / 100 °C / Inert atmosphere
9: water; lithium hydroxide monohydrate / 1,4-dioxane / 22.5 h / 110 °C
10: ChiralPak IC / ethanol / Resolution of racemate
With
lithium hydroxide monohydrate; Bromoform; sulfuric acid; N-benzyl-N,N,N-triethylammonium chloride; water; sodium hydrogencarbonate; potassium carbonate; ammonium chloride; sodium hydroxide; tri tert-butylphosphoniumtetrafluoroborate; zinc;
tris-(dibenzylideneacetone)dipalladium(0);
In
1,4-dioxane; pyridine; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetone; toluene;