Sodium Hydroxide → (1RS,2SR)-1-(4-fluorophenyl)-2-(methylamino)-3-(4-(trifluoromethyl)phenyl)-1-propanol

HRID 1610248Notes

Reaction equation

HRID 1610248 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12][C:11](=O)[N:10](C)[CH:9]2[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:12])[CH:9]([NH:10][CH3:11])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22261850(4RS,5SR)-5-(4-fluorophenyl)-3-methyl-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one

Product 1

HCID 22261511(1RS,2SR)-1-(4-fluorophenyl)-2-(methylamino)-3-(4-(trifluoromethyl)phenyl)-1-propanolYield 79%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of (4RS,5SR)-5-(4-fluorophenyl)-3-methyl-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one (4.56 g, 12.9 mmol) in ethanol (20 ml) was added 8N aqueous sodium hydroxide solution (8.07 ml) and the mixture was heated under reflux for 3 hrs. The reaction solution was diluted with water (200 ml) and extracted with ethyl acetate (200 ml×2). The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was recrystallized from diisopropyl ether-hexane to give (1RS,2SR)-1-(4-fluorophenyl)-2-(methylamino)-3-(4-(trifluoromethyl)phenyl)-1-propanol (3.34 mg, 79%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hrs
  3. extractionextracted with ethyl acetate (200 ml×2)
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was recrystallized from diisopropyl ether-hexane

Sources & evidence

ORD record
ord-601f7dfa8a58436e864b5694e357d5a9
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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