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

HRID 1610424Notes

Reaction equation

HRID 1610424 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH:6]2[O:10]C(=O)[NH:8][CH:7]2[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)=[CH:2]1.[OH-].[Na+]>C(O)C>[NH2:8][CH:7]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:20])[F:21])=[CH:15][CH:14]=1)[CH:6]([C:3]1[CH:4]=[CH:5][O:1][CH:2]=1)[OH:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22261716(4RS,5SR)-5-(3-furanyl)-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one

Product 1

HCID 22262061(1RS,2SR)-2-amino-1-(3-furanyl)-3-(4-(trifluoromethyl)phenyl)-1-propanolYield 86.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (4RS,5SR)-5-(3-furanyl)-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one (7.0 g, 22.5 mmol) in ethanol (100 ml) was added 8N aqueous sodium hydroxide solution (14.0 ml, 112.5 mmol) and the mixture was heated under reflux for 3 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-furanyl)-3-(4-(trifluoromethyl)phenyl)-1-propanol (5.54 g, 86%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 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-8ce46f2ddf9745a6a89b863320dd3b8f
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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