Ammonium formate → 1-[3-(Methoxycarbonyl)phenyl]nipecotic acid

HRID 602171Notes

Reaction equation

HRID 602171 reaction equation
[CH:1]([O-:3])=[O:2].[NH4+:4].N1CCCC(C(OCC2([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([O:26][CH3:27])=[O:25])[CH:19]=3)C=CC=CC2)=O)C1>[Pd].CO>[CH3:27][O:26][C:24]([C:20]1[CH:19]=[C:18]([N:4]2[CH2:22][CH2:23][CH2:18][CH:19]([C:1]([OH:3])=[O:2])[CH2:20]2)[CH:23]=[CH:22][CH:21]=1)=[O:25]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 866158861-[3-(Methoxycarbonyl)phenyl]benzyl nipecotate

Product 1

HCID 589926191-[3-(Methoxycarbonyl)phenyl]nipecotic acidYield 180.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In an argon atmosphere, 10% palladium on activated carbon (234 mg) and ammonium formate (1.66 g, 26.4 mmol) were added to 1-[3-(methoxycarbonyl)phenyl]benzyl nipecotate (2.34 g, 6.60 mmol) in methanol (50 mL). The reaction mixture was stirred at room temperature for 4 hours. Subsequently, the mixture was filtered through Celite and the filtrate was concentrated. 5% aqueous citric acid was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was then washed with brine and was dried over sodium sulfate. The solvent was evaporated to give 1.57 g (90%) of the desired compound as a pale reddish brown powder.

Workup

  1. filtrationSubsequently, the mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. addition5% aqueous citric acid was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was then washed with brine
  6. dry with materialwas dried over sodium sulfate
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-63aedc74330e42e6bd361332d1b1bf94
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Reaction notes

Loading…