Sodium Hydroxide → HCID 22261640, compound

HRID 1610766Notes

Reaction equation

HRID 1610766 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:16]=[CH:17][C:18]3[O:22][CH2:21][C:20]([CH3:24])([CH3:23])[C:19]=3[CH:25]=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]2[O:22][CH2:21][C:20]([CH3:23])([CH3:24])[C:19]=2[CH:25]=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 22262241HCID 22262241, compound

Product 1

HCID 22261640HCID 22261640, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of (4RS,5SR)-5-(3-chlorophenyl)-4-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl)methyl]-1,3-oxazolidin-2-one (5.33 g, 14.9 mmol) in ethanol (100 ml) was added 8N aqueous sodium hydroxide solution (9.3 ml, 74.5 mmol), and the mixture was heated under reflux for 5 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 and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by recrystallization (hexane-ethyl acetate) to give (1RS,2SR)-2-amino-1-(3-chlorophenyl)-3-(3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-1-propanol (3.68 g, 74%) 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. extractionthe mixture was extracted with ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customthe residue was purified by recrystallization (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-9aa96b2728b64f158330478931c77524
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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