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

HRID 1610397Notes

Reaction equation

HRID 1610397 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[O:13]C(=O)[NH:11][CH:10]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:5]=[CH:6][C:7]=1[F:8].[OH-].[Na+]>C(O)C>[NH2:11][CH:10]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1)[CH:9]([C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=1)[OH:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22262092HCID 22262092, compound

Product 1

HCID 22261782(1RS,2SR)-2-amino-1-(3,4-difluorophenyl)-3-(4-(trifluoromethyl)phenyl)-1-propanolYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (4RS,5SR)-5-(3,4-difluorophenyl)-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one (3.5 g, 9.8 mmol) in ethanol (60 ml) was added 8N aqueous sodium hydroxide solution (6.1 ml, 49 mmol) and the mixture was heated under reflux for 6 hrs. The reaction solution was concentrated, diluted with water (300 ml), and extracted with ethyl acetate (300 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give (1RS,2SR)-2-amino-1-(3,4-difluorophenyl)-3-(4-(trifluoromethyl)phenyl)-1-propanol (2.43 g, 75%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hrs
  3. concentrationThe reaction solution was concentrated
  4. additiondiluted with water (300 ml)
  5. extractionextracted with ethyl acetate (300 ml×2)
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated under reduced pressure
  9. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b9537d65b4a84f6e8254441d21c4a76f
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

Loading…