Water → (R)-N-((2-(2,2-Dimethoxypropyl)phenyl)(4-(trifluoromethyl)phenyl)-methyl)-2-methylpropane-2-sulfinamide

HRID 445360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 445360
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:13][CH3:14])([O:11][CH3:12])[CH3:10].C([Li])(C)(C)C.[F:20][C:21]([F:37])([F:36])[C:22]1[CH:35]=[CH:34][C:25]([CH:26]=[N:27][S@@:28]([C:30]([CH3:33])([CH3:32])[CH3:31])=[O:29])=[CH:24][CH:23]=1.O>C1COCC1>[CH3:12][O:11][C:9]([O:13][CH3:14])([CH3:10])[CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:26]([C:25]1[CH:24]=[CH:23][C:22]([C:21]([F:36])([F:37])[F:20])=[CH:35][CH:34]=1)[NH:27][S@@:28]([C:30]([CH3:33])([CH3:32])[CH3:31])=[O:29]

Komponenten

6

Edukt 4

HCID 962WaterHCID 595364291-Bromo-2-(2,2-dimethoxypropyl)benzeneHCID 68498575(R)-N-(4-(trifluoromethyl)benzylidene)-2-methylpropane-2-sulfinamideHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 59536312(R)-N-((2-(2,2-Dimethoxypropyl)phenyl)(4-(trifluoromethyl)phenyl)-methyl)-2-methylpropane-2-sulfinamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

1-Bromo-2-(2,2-dimethoxypropyl)benzene (4.00 g, 15.43 mmol) was dissolved in 150 mL THF and tert-butyllithium (18.160 mL, 30.871 mmol) was added dropwise at −78° C. After addition a solution of (R)—N-(4-(trifluoromethyl)-benzylidene)-2-methylpropane-2-sulfinamide (8.5608 g, 30.871 mmol) in THF (10 mL) was added and stirring was continued for 10 min in the cold. The reaction was hydrolyzed with 50 mL water and the mixture was warmed to RT. TLC showed a 1:1 mixture of the 2 diastereomers. No attempt was undertaken to separate the isomers. Glass column chromatography provided the title compound as a mixture of diastereomers. MS (ESI, positive ion) m/z: 412.0 (M+1; hydrolysis of the dimethyl acetal to the corresponding ketone).

Aufarbeitung

  1. additionwas added
  2. additiona 1:1 mixture of the 2 diastereomers
  3. customto separate the isomers

Quellen und Nachweise

ORD-Eintrag
ord-f3360a77b88b4df1b31c508ff3b4e934
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476297B2

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