HCID 86732257, Verbindung → HCID 86732258, Verbindung
Reaktionsgleichung
[CH3:1][C:2]([S@:5]([NH:7][C@:8]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=1[F:25])([CH2:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:9][F:10])=[O:6])([CH3:4])[CH3:3]>CC(O)C>[CH3:4][C:2]([S@:5]([NH:7][C@:8]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=1[F:25])([CH2:11][C@H:12]([OH:17])[C:13]([F:15])([F:14])[F:16])[CH2:9][F:10])=[O:6])([CH3:1])[CH3:3]Komponenten
3
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Ru[p-cymeme](1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (2.365 g, 3.94 mmol) was added in one portion to a solution of (R)-2-methyl-N-((S)-1,5,5,5-tetrafluoro-2-(2-fluoro-3-methylphenyl)-4-oxopentan-2-yl)propane-2-sulfinamide (3.80 g, 9.86 mmol) in IPA (100 ml) (which had been degassed by bubbling nitrogen through the solution for 30 minutes prior to use) under N2 atmosphere. The reaction was stirred at rt for 2 h. The reaction went to completion. The reaction was quenched with saturated NaHCO3, extracted with EtOAc and the combined organic extracts were washed with water, brine, dried over Na2SO4, filtered, concentrated and chromatographed on silica gel using 0-40% EtOAc/hexanes to afford a light brown solid as (R)-2-methyl-N-((2S,4S)-1,5,5,5-tetrafluoro-2-(2-fluoro-3-methylphenyl)-4-hydroxypentan-2-yl)propane-2-sulfinamide (2.0 g, 5.16 mmol, 52.4% yield). MS m/z=387.9 [M+H]+. Calculated for C16H22F5NO2S: 387.13.