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

HRID 1610476Notes

Reaction equation

HRID 1610476 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]2[CH:13]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[O:12]C(=O)[NH:10]2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[NH2:10][CH:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[CH:13]([C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:16][CH:15]=1)[OH:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22261770(4RS,5SR)-4-((4-fluorophenyl)methyl)-5-(4-(trifluoromethyl)phenyl)-1,3-oxazolidin-2-one

Product 1

HCID 22261902(1RS,2SR)-2-amino-3-(4-fluorophenyl)-1-(4-(trifluoromethyl)phenyl)-1-propanolYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (4RS,5SR)-4-((4-fluorophenyl)methyl)-5-(4-(trifluoromethyl)phenyl)-1,3-oxazolidin-2-one (18 g, 53.1 mmol) in ethanol (300 ml) was added 8N aqueous sodium hydroxide solution (19.9 ml, 159 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. Recrystallization of the residue from ethyl acetate-hexane gave (1RS,2SR)-2-amino-3-(4-fluorophenyl)-1-(4-(trifluoromethyl)phenyl)-1-propanol (14.1 g, 85%).

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. customRecrystallization of the residue from ethyl acetate-hexane

Sources & evidence

ORD record
ord-1643c343355c4bba880d7c1b4c86c503
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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