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

HRID 445360Notes

Reaction equation

HRID 445360 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-f3360a77b88b4df1b31c508ff3b4e934
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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