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

HRID 445360ノート

反応式

HRID 445360 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-f3360a77b88b4df1b31c508ff3b4e934
出典データセット
uspto-grants-2013_07
特許番号
US08476297B2

反応ノート

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