Sodium Hydroxide → (1RS,2RS)-1-(4-fluorophenyl)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)-2-propylamine

HRID 1610188Notes

Reaction equation

HRID 1610188 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12]C(=O)[NH:10][CH:9]2[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O>[NH2:10][CH:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:17][CH:16]=1)[CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[OH:12]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22262143(4RS,5RS)-5-(4-fluorophenyl)-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one

Product 1

HCID 22261479(1RS,2RS)-1-(4-fluorophenyl)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)-2-propylamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

(4RS,5SR)-5-(4-Fluorophenyl)-4-[4-(trifluoromethyl)benzyl]-1,3-oxazolidin-2-one (18.75 g, 55.26 mmol) and sodium hydroxide (8.84 g, 221 mmol) were heated under reflux in ethanol (100 ml)-water (10 ml) for 5 hrs. The reaction solution was diluted with water and extracted twice with ethyl acetate. The collected organic-layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel (APS type) column chromatography (hexane/ethyl acetate=1/1-ethyl acetate) and crystallized from diethyl ether-hexane to give the objective substance.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe collected organic-layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel (APS type) column chromatography (hexane/ethyl acetate=1/1-ethyl acetate)
  5. customcrystallized from diethyl ether-hexane
  6. customto give the objective substance

Sources & evidence

ORD record
ord-c988838527ac4713be4d2c1d7c977011
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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