4-Methyl-5-phenyl-2-oxazolidinone, (4S,5R)- → (4S,5R)-3-(2-Bromo-5-trifluoromethyl-benzyl)-4-methyl-5-phenyl-oxazolidin-2-one

HRID 456204ノート

反応式

HRID 456204 の反応式
[CH3:1][C@H:2]1[C@@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4](=[O:13])[NH:3]1.C([Li])CCC.[Br:19][C:20]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][C:21]=1[CH2:22]Br>>[Br:19][C:20]1[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:24][C:21]=1[CH2:22][N:3]1[C@@H:2]([CH3:1])[C@@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4]1=[O:13]

参加物

4

反応物 3

HCID 8531614-Methyl-5-phenyl-2-oxazolidinone, (4S,5R)-HCID 27562491-Bromo-2-(bromomethyl)-4-(trifluoromethyl)benzeneHCID 178418339Butyllithium

生成物 1

HCID 66890163(4S,5R)-3-(2-Bromo-5-trifluoromethyl-benzyl)-4-methyl-5-phenyl-oxazolidin-2-one

反応条件

温度
-78 °C

実験手順

To (4S,5R)-(−)-4-methyl-5-phenyl-2-oxazolidinone (0.386 g, 2.13 mmol) in THY (7 mL) at −78° C. under N2 was added n-butyllithium (2.5M in hexanes; 0.94 mL, 2.35 mmol), and the mixture was stirred at −78° C. for 30 minutes. 2-Bromo-5-(trifluoromethyl)benzyl bromide (0.678 g, 2.13 mmol) was added, and the reaction was warmed to room temperature and stirred overnight. Once no starting material was seen by analytical LCMS, the mixture was transferred to a separatory funnel and partitioned between EtOAc and H2O. The organic layer was separated and washed with brine, dried over MgSO4, filtered, and concentrated to give the title compound.

後処理

  1. temperaturethe reaction was warmed to room temperature
  2. stirringstirred overnight
  3. customthe mixture was transferred to a separatory funnel
  4. custompartitioned between EtOAc and H2O
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-0dcd10a379fe4d3988482eab28883d73
出典データセット
uspto-grants-2013_07
特許番号
US08497381B2

反応ノート

読み込み中…