Sodium Hydroxide → HCID 22262202, compound

HRID 1610364Notes

Reaction equation

HRID 1610364 reaction equation
[C:1]1([CH:7]2[O:11]C(=O)[NH:9][CH:8]2[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[NH2:9][CH:8]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:18][CH:19]=1)[CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[OH:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22261980HCID 22261980, compound

Product 1

HCID 22262202HCID 22262202, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (4RS,5SR)-5-phenyl-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one (6.0 g, 18.7 mmol) in ethanol (100 ml) was added 8N aqueous sodium hydroxide solution (11.7 ml, 93 mmol) and the mixture was heated under reflux for 4 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 diisopropyl ether-hexane to give (1RS,2SR)-2-amino-1-phenyl-3-(4-(trifluoromethyl)phenyl)-1-propanol (4.8 g, 87%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 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 diisopropyl ether-hexane

Sources & evidence

ORD record
ord-8c87c1430b6a427eab0046eb92477723
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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