HCID 68884278, compound → (S)-2-[3-[1-[(4-Isopropylphenyl)acetyl]piperidin-3-yl]phenoxy]-2-methylpropionic acid

HRID 1269499Notes

Reaction equation

HRID 1269499 reaction equation
C([O:8][C:9](=[O:38])[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:37])[CH2:27][C:28]3[CH:33]=[CH:32][C:31]([CH:34]([CH3:36])[CH3:35])=[CH:30][CH:29]=3)[CH2:21]2)[CH:15]=1)([CH3:12])[CH3:11])C1C=CC=CC=1>[Pd].CO>[CH:34]([C:31]1[CH:32]=[CH:33][C: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:38])=[O:8])[CH2:21]2)=[O:37])=[CH:29][CH:30]=1)([CH3:36])[CH3:35]

Participants

4

Reactant 1

HCID 68884278HCID 68884278, compound

Product 1

HCID 10047934(S)-2-[3-[1-[(4-Isopropylphenyl)acetyl]piperidin-3-yl]phenoxy]-2-methylpropionic acidYield 78.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (50 mg, 10 wt %) was added to a solution of 2-(3-{1-[(4-isopropyl-phenyl)-acetyl]-piperidin-3-yl}-phenoxy)-2-methyl-propionic acid benzyl ester (494 mg, 0.96 mmol) in methanol (15 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 319 mg (78%) of 2-(3-{1-[(4-Isopropyl-phenyl)-acetyl]-piperidin-3-yl}-phenoxy)-2-methyl-propionic acid as a clear oil.

Workup

  1. filtrationThe reaction mixture was filtered through a plug of celite
  2. washthe celite plug washed thoroughly with ethyl acetate
  3. concentrationThe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-d927f9406a9b4b1fae2ee4b0e1808742
Source dataset
uspto-grants-2007_04
Patent number
US07199243B2

Reaction notes

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