Sodium Hydroxide → (1RS,2SR)-2-amino-1-(4-(phenyloxy)phenyl)-3-(3-((1,1,2,2-tetrafluoroethyl)oxy)phenyl)-1-propanol

HRID 1610485Notes

Reaction equation

HRID 1610485 reaction equation
[C:1]1([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]3[O:18]C(=O)[NH:16][CH:15]3[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]([F:33])([F:32])[CH:29]([F:31])[F:30])[CH:22]=3)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[NH2:16][CH:15]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]([F:32])([F:33])[CH:29]([F:30])[F:31])[CH:22]=1)[CH:14]([C:11]1[CH:10]=[CH:9][C:8]([O:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:13][CH:12]=1)[OH:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22262036(4RS,5SR)-5-(4-(phenyloxy)phenyl)-4-((3-((1,1,2,2-tetrafluoroethyl)oxy)phenyl)methyl)-1,3-oxazolidin-2-one

Product 1

HCID 22261513(1RS,2SR)-2-amino-1-(4-(phenyloxy)phenyl)-3-(3-((1,1,2,2-tetrafluoroethyl)oxy)phenyl)-1-propanolYield 87.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (4RS,5SR)-5-(4-(phenyloxy)phenyl)-4-((3-((1,1,2,2-tetrafluoroethyl)oxy)phenyl)methyl)-1,3-oxazolidin-2-one (3.7 g, 8.02 mmol) in ethanol (10 ml) was added 8N aqueous sodium hydroxide solution (5.0 ml, 40 mmol), and the mixture was heated under reflux for 4 hrs. The reaction solution was concentrated, diluted with water (100 ml) and extracted with ethyl acetate (100 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. Recrystallization of the residue from ethyl acetate-hexane gave (1RS,2SR)-2-amino-1-(4-(phenyloxy)phenyl)-3-(3-((1,1,2,2-tetrafluoroethyl)oxy)phenyl)-1-propanol (3.05 g, 87%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hrs
  3. concentrationThe reaction solution was concentrated
  4. additiondiluted with water (100 ml)
  5. extractionextracted with ethyl acetate (100 ml×2)
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated under reduced pressure
  9. customRecrystallization of the residue from ethyl acetate-hexane

Sources & evidence

ORD record
ord-53a8e88fd4884294a4e4550a84dd49b5
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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