Multi-step reaction with 6 steps
1.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1.17 h / 0 °C / Inert atmosphere
2.1: phosphorus tribromide / diethyl ether / 2 h / 0 °C / Inert atmosphere
3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere
3.2: 1 h / 0 °C / Inert atmosphere
4.1: toluene; 1,4-dioxane / 10 h / Sealed tube
5.1: 1,1,1,3',3',3'-hexafluoro-propanol; 1-(3,5-bis(trifluoromethyl)phenyl)-3-((R)-quinolin-4-yl((1S,2R,4S,5R)-5-vinylquinu clidin-2-yl)methyl)thiourea / dichloromethane / -70 °C
6.1: hydrogenchloride / ethyl acetate / 9 h / 0 °C / Inert atmosphere
With
hydrogenchloride; 1-(3,5-bis(trifluoromethyl)phenyl)-3-((R)-quinolin-4-yl((1S,2R,4S,5R)-5-vinylquinu clidin-2-yl)methyl)thiourea; 1,1,1,3',3',3'-hexafluoro-propanol; phosphorus tribromide; sodium hydride; diisobutylaluminium hydride;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; mineral oil;
4.1: |Aza-Wittig Reaction;
DOI:10.1039/c2cc36665g