1-(3-Phenyl-propionyl)-piperidine-4-carboxylic acid benzyl ester → 1-(3-Phenylpropanoyl)piperidine-4-carboxylic acid

HRID 1177875Notes

Reaction equation

HRID 1177875 reaction equation
C([O:8][C:9]([CH:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:26])[CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:13][CH2:12]1)=[O:10])C1C=CC=CC=1.[H][H]>CO.[Pd]>[C:20]1([CH2:19][CH2:18][C:17]([N:14]2[CH2:13][CH2:12][CH:11]([C:9]([OH:10])=[O:8])[CH2:16][CH2:15]2)=[O:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 595596251-(3-Phenyl-propionyl)-piperidine-4-carboxylic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 28131931-(3-Phenylpropanoyl)piperidine-4-carboxylic acidYield 59.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd/c (528 mg) was added to a stirred solution of 1-(3-phenyl-propionyl)-piperidine-4-carboxylic acid benzyl ester (2.64 gm, 7.5 mmol) in MeOH (52.8 mL) and continued the stirring under hydrogen atmosphere for 3 hrs. The mixture was filtered over a bed of celite. The celite was washed with MeOH and the filtrate was concentrated under reduced pressure to afford 1.17 g (59.6% yield) of 1-(3-phenyl-propionyl)-piperidine-4-carboxylic acid. LCMS Purity: 93.56%.

Workup

  1. customfor 3 hrs
  2. filtrationThe mixture was filtered over a bed of celite
  3. washThe celite was washed with MeOH
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3ff8eea3439b4e4fae466334a638a7c3
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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