Sodium Hydroxide → (1RS,2SR)-2-amino-1-(3-chlorophenyl)-3-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]propan-1-ol

HRID 1610556Notes

Reaction equation

HRID 1610556 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][CH:18]=[C:17]([O:21][C:22]([F:27])([F:26])[CH:23]([F:25])[F:24])[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:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]([F:27])([F:26])[CH:23]([F:25])[F:24])[CH:16]=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 22262011HCID 22262011, compound

Product 1

HCID 22261910(1RS,2SR)-2-amino-1-(3-chlorophenyl)-3-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]propan-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (4RS,5SR)-5-(3-chlorophenyl)-4-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]-1,3-oxazolidin-2-one (3.70 g, 9.16 mmol) in ethanol (30 ml) was added 8N aqueous sodium hydroxide solution (5.7 ml, 46 mmol), and the mixture was heated under reflux for 3 hrs. The reaction solution was concentrated and diluted with water (100 ml). The mixture was extracted with ethyl acetate (100 ml×2). The extract was washed with saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure to give the objective substance (3.0 g, 87%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hrs
  3. concentrationThe reaction solution was concentrated
  4. additiondiluted with water (100 ml)
  5. extractionThe mixture was extracted with ethyl acetate (100 ml×2)
  6. washThe extract was washed with saturated brine
  7. dry with materialdried (anhydrous magnesium sulfate)
  8. customevaporated under reduced pressure
  9. customto give the objective substance (3.0 g, 87%)

Sources & evidence

ORD record
ord-ae59aa6a62f94268903780348dbb3f5f
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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