Multi-step reaction with 18 steps
1.1: sodium periodate; silica gel / dichloromethane; water / 1 h / 20 °C / Inert atmosphere
2.1: (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine / dichloromethane / 36 h / 4 °C
2.2: -5 °C
3.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere
3.2: 1.5 h / -78 °C / Inert atmosphere
4.1: 20 % Pd(OH)2/C; hydrogen / ethyl acetate / 6 h / 20 °C / Inert atmosphere
5.1: pyridine; dmap / 0.75 h / 0 - 20 °C / Inert atmosphere
6.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere
6.2: 12 h / -65 °C / Inert atmosphere
7.1: sodium tetrahydroborate / methanol / 2 h / 20 °C / Cooling with ice; Inert atmosphere
8.1: pyridine / 1.5 h / 0 - 20 °C / Inert atmosphere
9.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere
10.1: methanesulfonamide; hydroquinidein 1,4-phthalazinediyl diether / water; tert-butyl alcohol / 72 h / 4 °C / Inert atmosphere
11.1: Trimethyl orthoacetate; pyridinium p-toluenesulfonate / dichloromethane / 5 h / 20 °C / Inert atmosphere
11.2: 3 h / 20 °C / Inert atmosphere
11.3: 2 h / 20 °C / Inert atmosphere
12.1: diisobutylaluminium hydride / hexane; toluene / 0.33 h / -78 °C / Inert atmosphere
13.1: N,N-dimethyl-formamide / 4 h / Reflux; Inert atmosphere
14.1: dmap; triethylamine / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
15.1: hydrogenchloride; methanol / 5 h / 20 °C / Inert atmosphere
16.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C / Inert atmosphere
16.2: -78 - 0 °C / Inert atmosphere
17.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
17.2: 0.5 h / 0 °C
18.1: methanol; potassium carbonate / 1.5 h / 20 °C / Inert atmosphere
With
pyridine; (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; hydrogenchloride; methanol; Trimethyl orthoacetate; dmap; sodium tetrahydroborate; sodium periodate; n-butyllithium; oxalyl dichloride; methanesulfonamide; 20 % Pd(OH)2/C; potassium tert-butylate; hydrogen; pyridinium p-toluenesulfonate; silica gel; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; diisopropylamine; N,N-dimethyl-formamide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; toluene; tert-butyl alcohol;
3.1: Peterson olefination / 3.2: Peterson olefination / 16.1: Swern oxidation / 16.2: Swern oxidation / 17.1: Wittig reaction / 17.2: Wittig reaction;
DOI:10.1016/j.tetlet.2010.12.066