Sodium Hydroxide → HCID 22261660, compound

HRID 1610381Notes

Reaction equation

HRID 1610381 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[O:12]C(=O)[NH:10][CH:9]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1.[OH-].[Na+]>C(O)C>[NH2:10][CH:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:17][CH:16]=1)[CH:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])[OH:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22261747HCID 22261747, compound

Product 1

HCID 22261660HCID 22261660, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (4RS,5SR)-5-(2-fluorophenyl)-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one (7.0 g, 20.6 mmol) in ethanol (100 ml) was added 8N aqueous sodium hydroxide solution (12.9 ml, 103 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 purified by silica gel column chromatography (ethyl acetate) to give (1RS,2SR)-2-amino-1-(2-fluorophenyl)-3-(4-(trifluoromethyl)phenyl)-1-propanol (6.2 g, 96%) as a colorless oil.

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 purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-126e8c76ef544ea6a4daa3758ea1dfe7
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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