Multi-step reaction with 12 steps
1.1: sodium hydride / 0.33 h / 20 - 80 °C
2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / -78 - 20 °C
3.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dichloromethane; water; N,N-dimethyl-formamide / 20 °C
4.1: methanol; magnesium / Heating / reflux
5.1: sodium methylate / methanol / Heating / reflux
6.1: lithium hydroxide; water / tetrahydrofuran; methanol / 20 °C
6.2: pH 1
7.1: diphenyl phosphoryl azide; triethylamine / toluene / 48 h / 20 - 90 °C
8.1: Resolution of racemate
9.1: sulfuric acid / 1,4-dioxane; water / 1 h / 20 °C
10.1: decaborane / methanol / 18 h
11.1: hydrogenchloride / 1,4-dioxane; ethyl acetate; isopropyl alcohol / 0.17 h
11.2: 2 h
12.1: caesium carbonate / 1 h / 20 °C
With
hydrogenchloride; methanol; lithium hydroxide; decaborane; sulfuric acid; diphenyl phosphoryl azide; water; sodium methylate; sodium hydride; sodium carbonate; caesium carbonate; magnesium; triethylamine; N-ethyl-N,N-diisopropylamine;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; toluene;
7.1: Curtius Rearrangement;