Sodium Hydroxide → (1RS,2SR)-2-amino-1-[4-(benzyloxy)phenyl]-3-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]propan-1-ol

HRID 1610548Notes

Reaction equation

HRID 1610548 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[O:19]C(=O)[NH:17][CH:16]2[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:34])([F:33])[CH:30]([F:32])[F:31])[CH:23]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[NH2:17][CH:16]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:33])([F:34])[CH:30]([F:31])[F:32])[CH:23]=1)[CH:15]([C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1)[OH:19]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22262007(4RS,5SR)-5-[4-(benzyloxy)phenyl]-4-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]-1,3-oxazolidin 2-one

Product 1

HCID 22261439(1RS,2SR)-2-amino-1-[4-(benzyloxy)phenyl]-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-[4-(benzyloxy)phenyl]-4-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]-1,3-oxazolidin-2-one (2.50 g, 5.26 mmol) in ethanol (30 ml) was added 8N aqueous sodium hydroxide solution (2 ml, 16 mmol), and the mixture was heated under reflux for 5 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 (2.4 g, 100%)

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 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 (2.4 g, 100%)

Sources & evidence

ORD record
ord-09d2fa5d5d5640adb45f60e6a7420e0e
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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