Multi-step reaction with 10 steps
1.1: (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; benzoic acid / chloroform / 22 h / -50 °C / Inert atmosphere
2.1: sodium dihydrogenphosphate; sodium chlorite; dihydrogen peroxide / methanol; water; acetonitrile / 3 h / 0 - 20 °C / Inert atmosphere
3.1: methanol / diethyl ether; toluene / 3 h / 0 - 20 °C / Inert atmosphere
4.1: lithium diisopropyl amide / diethyl ether / 1 h / -100 °C / Inert atmosphere
4.2: 1 h / -100 °C / Inert atmosphere
5.1: dimethylsulfide borane complex / hexane / 0 °C / Inert atmosphere
5.2: 1 h / Inert atmosphere; Reflux
6.1: triethylamine / dichloromethane / 2 h / Inert atmosphere
7.1: 1.5 h / 20 °C / Inert atmosphere
8.1: sodium hydroxide / dichloromethane; water / Inert atmosphere
9.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 4 h / 0 - 20 °C / Inert atmosphere
10.1: diphenyl phosphoryl azide; triethylamine / toluene / Inert atmosphere; Reflux
10.2: 0.5 h / Inert atmosphere
With
(S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; methanol; sodium chlorite; sodium dihydrogenphosphate; lithium hydroxide monohydrate; dimethylsulfide borane complex; diphenyl phosphoryl azide; dihydrogen peroxide; triethylamine; benzoic acid; sodium hydroxide; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; chloroform; water; toluene; acetonitrile;
1.1: aza-Michael reaction;
DOI:10.1016/j.tet.2011.07.017