Ethyl Acetate → (4S,5R)-5-(3,5-Bis-trifluoromethyl-phenyl)-3-(2-bromo-5-trifluoromethyl-benzyl)-4-methyl-oxazolidin-2-one

HRID 456219Notes

Reaction equation

HRID 456219 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[NH:15][C@H:14]2[CH3:19])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C[Si](C)(C)N[Si](C)(C)C.[Na].[Br:32][C:33]1[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][C:34]=1[CH2:35]Br.CCOC(C)=O>C1COCC1.O>[F:21][C:2]([F:1])([F:20])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:35][C:34]3[CH:37]=[C:38]([C:41]([F:42])([F:44])[F:43])[CH:39]=[CH:40][C:33]=3[Br:32])[C@H:14]2[CH3:19])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 27562491-Bromo-2-(bromomethyl)-4-(trifluoromethyl)benzeneHCID 23583229(4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-oneHCID 45051731Sodium hexamethyidisilazane

Product 1

HCID 86650342(4S,5R)-5-(3,5-Bis-trifluoromethyl-phenyl)-3-(2-bromo-5-trifluoromethyl-benzyl)-4-methyl-oxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To (4S,5R)-5-(3,5-bis-trifluoromethyl-phenyl)-4-methyl-oxazolidin-2-one (0.246 g, 0.79 mmol) in THF (10 mL) at mom temperature was added sodium hexamethyldisilazane (1M in THF; 1.02 mL, 1.02 mmol), and the reaction was stirred for 15 minutes. 2-Bromo-5-(trifluoromethyl)benzyl bromide (0.250 g, 0.79 mmol) was added, and the reaction was stirred overnight at room temperature. The mixture was worked-up with EtOAc and H2O, and the crude material was purified by silica gel chromatography to give the title compound.

Workup

  1. stirringthe reaction was stirred overnight at room temperature
  2. customthe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8cbfbc09ef2b4a38957e0139f357c329
Source dataset
uspto-grants-2013_07
Patent number
US08497381B2

Reaction notes

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