Sodium Hydroxide → 4,4,4-Trifluoro-3-((3-(3-(trifluoromethyl)phenyl)piperidin-1-yl)methyl)butanoic acid
Reaction equation
C([O:3][C:4](=[O:28])[CH2:5][CH:6]([CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][CH:14]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[CH2:13]1)[C:7]([F:10])([F:9])[F:8])C.[OH-].[Na+]>C(O)C>[F:10][C:7]([F:8])([F:9])[CH:6]([CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][CH:14]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:25])([F:26])[F:27])[CH:19]=2)[CH2:13]1)[CH2:5][C:4]([OH:28])=[O:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
In a 10 mL pear-shaped flask, 4,4,4-trifluoro-3-[3-(3-trifluoromethyl-phenyl)-piperidin-1-ylmethyl]-butyric acid ethyl ester (130 mg, 316 μmol) and NaOH (237 μl, 474 μmol) were combined with ethanol (6 ml) to give a colorless solution. The reaction mixture was heated at 90° C. and stirred for 30 min. The reaction mixture was concentrated and treated with a saturated solution of NaH2PO4 (20 ml) and extracted with ethyl acetate (2×30 ml). The combined organics were washed with brine and H2O, dried over MgSO4, filtered and concentrated to give 120 mg (99%) of 4,4,4-trifluoro-3-[3-(3-trifluoromethyl-phenyl)-piperidin-1-ylmethyl]-butyric acid as a waxy solid. MH+=384.
Workup
- customto give a colorless solution
- concentrationThe reaction mixture was concentrated
- additiontreated with a saturated solution of NaH2PO4 (20 ml)
- extractionextracted with ethyl acetate (2×30 ml)
- washThe combined organics were washed with brine and H2O
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-74445e613e054f73a856921ad92a1545
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388172B2
Reaction notes
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