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

HRID 1610271Notes

Reaction equation

HRID 1610271 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12]C(=O)[NH:10][CH:9]2[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[NH2:10][CH:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:22])[F:23])[CH:16]=1)[CH:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[OH:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22262229(4RS,5SR)-5-(4-fluorophenyl)-4-((3-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one

Product 1

HCID 22261995(1RS,2SR)-2-amino-1-(4-fluorophenyl)-3-(3-(trifluoromethyl)phenyl)-1-propanolYield 80.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (4RS,5SR)-5-(4-fluorophenyl)-4-((3-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one (4.0 g, 11.8 mmol) in ethanol (80 ml) was added 8N aqueous sodium hydroxide solution (7.4 ml, 59 mmol) and the mixture was heated under reflux for 4 hrs. The reaction solution was concentrated, diluted with water (100 ml) and extracted with ethyl acetate (100 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-(4-fluorophenyl)-3-(3-(trifluoromethyl)phenyl)-1-propanol (2.97 g, 80%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hrs
  3. concentrationThe reaction solution was concentrated
  4. additiondiluted with water (100 ml)
  5. extractionextracted with ethyl acetate (100 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-2cc3b818dd6143b8b8ce3bc75813863b
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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