Multi-step reaction with 12 steps
1.1: potassium hydroxide / ethanol; N,N-dimethyl-formamide / 1.25 h / -2 °C
2.1: palladium on carbon; formic acid; ammonium formate / methanol / 1 h
3.1: 2 h / 0 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.5 h / Reflux
5.1: diphenyl phosphoryl azide; triphenylphosphine; diethylazodicarboxylate / toluene / 9 h
6.1: potassium tert-butylate / tetrahydrofuran / 6 h / 0 °C
7.1: 1,1,1,3',3',3'-hexafluoro-propanol; trimethylsilyl trifluoromethanesulfonate; bis-[(trifluoroacetoxy)iodo]benzene / water / 1 h / 0 °C
8.1: hydrogenchloride / methanol / 0.5 h / 20 °C / Inert atmosphere
8.2: 16 h / 20 °C / Inert atmosphere
9.1: bis-[(trifluoroacetoxy)iodo]benzene / 2,2,2-trifluoroethanol / 0.5 h / 20 °C / Inert atmosphere
10.1: boron trifluoride diethyl etherate / dichloromethane / 7 h / 0 - 20 °C / Inert atmosphere
11.1: hydrogen bromide; acetic acid / dichloromethane / 36 h / 0 - 20 °C / Inert atmosphere
12.1: sodium methylate / tetrahydrofuran; methanol / 0.5 h / 0 °C / Inert atmosphere
With
hydrogenchloride; lithium aluminium tetrahydride; formic acid; 1,1,1,3',3',3'-hexafluoro-propanol; trimethylsilyl trifluoromethanesulfonate; diphenyl phosphoryl azide; palladium on carbon; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen bromide; ammonium formate; sodium methylate; acetic acid; triphenylphosphine; bis-[(trifluoroacetoxy)iodo]benzene; potassium hydroxide; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; 2,2,2-trifluoroethanol; water; N,N-dimethyl-formamide; toluene;
5.1: Mitsunobu reaction;
DOI:10.1039/c1ob05058c