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

HRID 1610748Notes

Reaction equation

HRID 1610748 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:22]=[CH:23][CH:24]=1)[CH2:8][CH:9]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[O:12]C(=O)[NH:10]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[NH2:10][CH:9]([CH2:8][C:7]1[CH:22]=[CH:23][CH:24]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=1)[CH:13]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=1)[OH:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22262235HCID 22262235, compound

Product 1

HCID 22261432(1RS,2SR)-2-amino-3-[3-(tert-butyl)phenyl]-1-(3-chlorophenyl)-1-propanolYield 55.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of (4RS,5SR)-4-[3-(tert-butyl)benzyl]-5-(3-chlorophenyl)-1,3-oxazolidin-2-one (2.36 g, 6.86 mmol) in ethanol (60 ml) was added 8N aqueous sodium hydroxide (4.3 ml, 34.3 mmol), and the mixture was heated under reflux for 5 hrs. After the completion of the reaction, ethanol was evaporated under reduced pressure. The residue 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-(tert-butyl)phenyl]-1-(3-chlorophenyl)-1-propanol (1.21 g, 55%) as colorless crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hrs
  3. customwas evaporated under reduced pressure
  4. additionThe residue was diluted with water
  5. extractionextracted 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-9413a7b966dc4904a9bd0de8bea384f2
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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