Multi-step reaction with 8 steps
1.1: sodium tetrahydroborate / methanol / 2 h / 0 °C
2.1: sulfuric acid / dichloromethane; water / 28 h / 0 °C
2.2: pH ~ 9
3.1: Chiralpak AD column / diethylamine; isopropyl alcohol / Resolution of racemate
4.1: hydrogen bromide / water; acetic acid / 8 h / Reflux
5.1: pyridine / dichloromethane / 1 h / -78 - 0 °C
6.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / 1,2-dichloro-ethane / Reflux
7.1: methanol / 1 h / Reflux
8.1: caesium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; N,N-dimethyl-formamide / 2 h / 90 °C / Inert atmosphere
With
pyridine; methanol; sodium tetrahydroborate; sulfuric acid; hydrogen bromide; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; caesium carbonate;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;
In
methanol; dichloromethane; water; acetic acid; 1,2-dichloro-ethane; diethylamine; N,N-dimethyl-formamide; isopropyl alcohol;