2-(3-{1-[3-(4-Isopropyl-phenyl)-acryloyl]-piperidin-3-yl}-phenoxy)-2-methyl-propionic acid benzyl ester → 2-(3-{1-[3-(4-Isopropyl-phenyl)-propionyl]-piperidin-3-yl}-phenoxy)-2-methyl-propionic acid
Reaction equation
C([O:8][C:9](=[O:39])[C:10]([O:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]2[CH2:25][CH2:24][CH2:23][N:22]([C:26](=[O:38])[CH:27]=[CH:28][C:29]3[CH:34]=[CH:33][C:32]([CH:35]([CH3:37])[CH3:36])=[CH:31][CH:30]=3)[CH2:21]2)[CH:15]=1)([CH3:12])[CH3:11])C1C=CC=CC=1>[Pd].CO>[CH:35]([C:32]1[CH:31]=[CH:30][C:29]([CH2:28][CH2:27][C:26]([N:22]2[CH2:23][CH2:24][CH2:25][CH:20]([C:16]3[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=3)[O:13][C:10]([CH3:11])([CH3:12])[C:9]([OH:39])=[O:8])[CH2:21]2)=[O:38])=[CH:34][CH:33]=1)([CH3:37])[CH3:36]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
10% Palladium on carbon (10 mg, 10 wt %) was added to a solution of 2-(3-{1-[3-(4-Isopropyl-phenyl)-acryloyl]-piperidin-3-yl}-phenoxy)-2-methyl-propionic acid benzyl ester (89 mg, 0.17 mmol) in methanol (2 mL) and the resulting mixture hydrogenated at atmospheric pressure for 3 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 to provide 73 mg (99%) of 2-(3-{1-[3-(4-Isopropyl-phenyl)-propionyl]-piperidin-3-yl}-phenoxy)-2-methyl-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
Sources & evidence
- ORD record
- ord-4d330071bc774defa75598cd4917ea4a
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199243B2
Reaction notes
Loading…