Trifluoroacetic acid → (1RS,2SR)-2-amino-1-(3-chlorophenyl)-3-[4-(2,2,3,3,3-pentafluoropropyl)phenyl]-1-propanol
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:33])[CH:9]([NH:25]C(=O)OC(C)(C)C)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[NH2:25][CH:9]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([F:24])([F:23])[C:19]([F:20])([F:21])[F:22])=[CH:13][CH:12]=1)[CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[OH:33]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of tert-butyl (1RS,2SR)-2-(3-chlorophenyl)-2-hydroxy-1-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]ethylcarbamate (2.00 g, 4.05 mmol) in chloroform (20 ml) was added trifluoroacetic acid (20 ml), and the mixture was stirred at room temperature for 1 hr. The mixture was concentrated under reduced pressure. To the residue was added water, and the mixture was basified with saturated aqueous sodium hydrogen carbonate. The aqueous layer was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated under the reduced pressure. The residue was recrystallized from (hexane-ethyl acetate) to give (1RS,2SR)-2-amino-1-(3-chlorophenyl)-3-[4-(2,2,3,3,3-pentafluoropropyl)phenyl]-1-propanol (1.08 g, 68%) as colorless crystals.
Workup
- concentrationThe mixture was concentrated under reduced pressure
- additionTo the residue was added water
- extractionThe aqueous layer was extracted with ethyl acetate
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under the reduced pressure
- customThe residue was recrystallized from (hexane-ethyl acetate)
Sources & evidence
- ORD record
- ord-9e1e35258b3d456f8db7a082431cf786
- Source dataset
- uspto-grants-2006_01
- Patent number
- US06982348B2
Reaction notes
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