4-Methyl-5-phenyl-2-oxazolidinone, (4S,5R)- → (4S,5R)-3-(2-Bromo-5-trifluoromethyl-benzyl)-4-methyl-5-phenyl-oxazolidin-2-one
Reaction equation
[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]Participants
4
Conditions
- Temperature
- -78 °C
Procedure
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.
Workup
- temperaturethe reaction was warmed to room temperature
- stirringstirred overnight
- customthe mixture was transferred to a separatory funnel
- custompartitioned between EtOAc and H2O
- customThe organic layer was separated
- washwashed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-0dcd10a379fe4d3988482eab28883d73
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08497381B2
Reaction notes
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