Sodium Hydroxide → (1RS,2SR)-2-amino-1-(3-chlorophenyl)-3-[4-(1,1-difluoro-2,2-dimethylpropyl)phenyl]-1-propanol

HRID 1610773Notes

Reaction equation

HRID 1610773 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[O:12]C(=O)[NH:10][CH:9]2[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:27])([F:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:17][CH:16]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>C(O)C>[NH2:10][CH:9]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]([F:27])([F:26])[C:22]([CH3:23])([CH3:24])[CH3:25])=[CH:19][CH:20]=1)[CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[OH:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22261594HCID 22261594, compound

Product 1

HCID 22261485(1RS,2SR)-2-amino-1-(3-chlorophenyl)-3-[4-(1,1-difluoro-2,2-dimethylpropyl)phenyl]-1-propanolYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of (4RS,5SR)-5-(3-chlorophenyl)-4-[4-(1,1-difluoro-2,2-dimethylpropyl)benzyl]-1,3-oxazolidin-2-one (3.82 g, 9.70 mmol) in ethanol (100 ml) was added 8N aqueous sodium hydroxide solution (6.1 ml, 48.5 mmol), and the mixture was heated under reflux for 4 hrs. After completion of the reaction, ethanol was evaporated under reduced pressure. The residue was diluted with water, and the mixture was extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by recrystallization (hexane-ethyl acetate) to give (1RS,2SR)-2-amino-1-(3-chlorophenyl)-3-[4-(1,1-difluoro-2,2-dimethylpropyl)phenyl]-1-propanol (2.56 g, 72%) to give colorless crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hrs
  3. customwas evaporated under reduced pressure
  4. additionThe residue was diluted with water
  5. extractionthe mixture was extracted with ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by recrystallization (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-5ac1a2a3a55444d8bd06cde87af0a2ec
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

Loading…