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

HRID 1610740Notes

Reaction equation

HRID 1610740 reaction equation
[CH2:1]([O:6][C:7]1[CH:8]=[C:9]([CH:24]=[CH:25][CH:26]=1)[CH2:10][CH:11]1[CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[O:14]C(=O)[NH:12]1)[C:2]([CH3:5])([CH3:4])[CH3:3].[OH-].[Na+]>C(O)C.O>[NH2:12][CH:11]([CH2:10][C:9]1[CH:24]=[CH:25][CH:26]=[C:7]([O:6][CH2:1][C:2]([CH3:5])([CH3:4])[CH3:3])[CH:8]=1)[CH:15]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=1)[OH:14]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22261600(4RS,5SR)-4-[3-(neopentyloxy)benzyl]-5-(3-chlorophenyl)-1,3-oxazolidin-2-one

Product 1

HCID 22261929(1RS,2SR)-2-amino-3-[3-(neopentyloxy)phenyl]-1-(3-chlorophenyl)-1-propanolYield 79.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of (4RS,5SR)-4-[3-(neopentyloxy)benzyl]-5-(3-chlorophenyl)-1,3-oxazolidin-2-one (4.0 g, 10.7 mmol) in ethanol (80 ml) was added 8N aqueous sodium hydroxide solution (6.7 ml, 53.5 mmol), and the mixture was heated under reflux for 5 hrs. After completion of the reaction, the mixture was diluted with water and 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-3-[3-(neopentyloxy)phenyl]-1-(3-chlorophenyl)-1-propanol (2.95 g, 79%) as colorless crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hrs
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by recrystallization (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-4759182d5da84b17afedb0658d152d43
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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