2-Methyl-2-{3-[1-(4-trifluoromethyl-benzylcarbamoyl)-piperidin-3-yl]-phenoxy}-propionic acid benzyl ester → 2-Methyl-2-{3-[1-(4-trifluoromethyl-benzylcarbamoyl)-piperidin-3-yl]-phenoxy}-propionic acid
Reaction equation
C([O:8][C:9](=[O:40])[C:10]([CH3:39])([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]2[CH2:24][CH2:23][CH2:22][N:21]([C:25](=[O:38])[NH:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=3)[CH2:20]2)[CH:14]=1)[CH3:11])C1C=CC=CC=1>[Pd].CO>[CH3:39][C:10]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]2[CH2:24][CH2:23][CH2:22][N:21]([C:25](=[O:38])[NH:26][CH2:27][C:28]3[CH:29]=[CH:30][C:31]([C:34]([F:36])([F:37])[F:35])=[CH:32][CH:33]=3)[CH2:20]2)[CH:14]=1)([CH3:11])[C:9]([OH:40])=[O:8]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
10% Palladium on carbon (53 mg, 50 wt %) was added to a solution of 2-methyl-2-{3-[1-(4-trifluoromethyl-benzylcarbamoyl)-piperidin-3-yl]-phenoxy}-propionic acid benzyl ester (111 mg, 0.226 mmol) in methanol (5 mL) and the resulting mixture hydrogenated at 50 psi for 4 h. The reaction mixture was filtered through a plug of celite and the celite plug washed thoroughly with ethyl acetate. The combined filtrates were concentrated under reduced pressure. The resultant oil was flash chromatographed with 2% methanol/chloroform to provide 46.6 mg (51%) of 2-methyl-2-{3-[1-(4-trifluoromethyl-benzylcarbamoyl)-piperidin-3-yl]-phenoxy}-propionic acid as a clear oil.
Workup
- filtrationThe reaction mixture was filtered through a plug of celite
- washthe celite plug washed thoroughly with ethyl acetate
- concentrationThe combined filtrates were concentrated under reduced pressure
- customchromatographed with 2% methanol/chloroform
Sources & evidence
- ORD record
- ord-ac6e1a4fe1c645608b99ab7a2257aa70
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199243B2
Reaction notes
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