Multi-step reaction with 7 steps
1: lithium borohydride / tetrahydrofuran / 16 h / 20 - 75 °C / Inert atmosphere
2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 2 h / 20 °C / Inert atmosphere
3: titanium(IV)isopropoxide / toluene / 12 h / 20 - 90 °C / Inert atmosphere
4: tetrahydrofuran; diethyl ether / 12 h / 0 - 20 °C / Inert atmosphere
5: hydrogenchloride / 1,4-dioxane; methanol / 0.5 h / 20 °C / Inert atmosphere
6: triethylamine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere
7: sodium iodide / N,N-dimethyl-formamide / 6 h / 20 - 90 °C / Inert atmosphere
With
hydrogenchloride; lithium borohydride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; titanium(IV)isopropoxide; triethylamine; sodium iodide;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm201628y