Trifluoroacetic acid → HCID 22262071, compound

HRID 1610434Notes

Reaction equation

HRID 1610434 reaction equation
[OH:1][CH:2]([C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1)[CH:3]([NH:15]C(=O)OC(C)(C)C)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1.FC(F)(F)C(O)=O>[OH-].[Na+]>[NH2:15][CH:3]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:12])[F:13])=[CH:7][CH:6]=1)[CH:2]([C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1)[OH:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86593250HCID 86593250, compound

Product 1

HCID 22262071HCID 22262071, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To 1,1-dimethylethyl (1RS,2SR)-2-hydroxy-2-(4-pyridyl)-1-((4-(trifluoromethyl)phenyl)methyl)ethylcarbamate (300 mg, 0.76 mmol) was added trifluoroacetic acid (3 ml), and the mixture was stirred at room temperature for 10 min. To the reaction solution was added 1N aqueous sodium hydroxide solution (10 ml) and the mixture was extracted with ethyl acetate (20 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate-diisopropyl ether to give (1RS,2SR)-2-amino-1-(4-pyridyl)-3-(4-(trifluoromethyl)phenyl)-1-propanol (135 mg, 60%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (20 ml×2)
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-1d490eb7eab14af2a96f9f7ba19b6192
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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