Multi-step reaction with 8 steps
1.1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 0 - 20 °C
2.1: hydrogenchloride / 1,4-dioxane / 15 h / 45 °C
3.1: acetic anhydride / 3 h / 90 °C
4.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane; water / 3 h / 90 °C / Inert atmosphere; Sealed tube
5.1: (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; zinc; palladium diacetate; sulfuric acid / N,N-dimethyl acetamide / 3.5 h / 100 °C / Inert atmosphere
6.1: 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere
6.2: 1.5 h / -78 - 20 °C / Inert atmosphere
7.1: sodium hydride / tetrahydrofuran / 0 °C / Inert atmosphere
7.2: 0 - 20 °C / Inert atmosphere
8.1: Chiralpak IC, 21×250 mm / carbon dioxide; isopropyl alcohol / Resolution of racemate; liquid CO2
With
hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex; sulfuric acid; palladium diacetate; acetic anhydride; sodium tris(acetoxy)borohydride; sodium hydride; caesium carbonate; acetic acid; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; zinc;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl acetamide; carbon dioxide; water; isopropyl alcohol;