Acetic Acid → HCID 70023968, compound

HRID 398382Notes

Reaction equation

HRID 398382 reaction equation
C([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[C:17]([CH3:19])[N:16]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:15](=[O:26])[CH:14]=2)[C@H:10]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:9]1)C1C=CC=CC=1.CC(O)=O>CCO.[Pd]>[C:27]1([C@H:10]2[C@@H:11]([C:13]3[CH:18]=[C:17]([CH3:19])[N:16]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:15](=[O:26])[CH:14]=3)[CH2:12][NH:8][CH2:9]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 70024691HCID 70024691, compound

Product 1

HCID 70023968HCID 70023968, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-(1-benzyl-cis-3-phenylpyrrolidin-4-yl)-6-methyl-1-ethoxycarbonylmethyl-2-pyridinone from step 5 above (0.30 g, 0.66 mmol), 10% Pd on carbon (100 mg), and HOAc (1 mL) in EtOH (10 mL) was stirred under an atmosphere of hydrogen at ambient pressure and temperature for 24 h. The catalyst was removed by filtration and the filtrate solvent was removed in vacuo. The residue was partitioned between CH2Cl2 and aqueous NaHCO3. The organic phase was separated, dried over MgSO4, filtered, and the solvent was removed in vacuo to give the title compound as an oil (0.2 g, HPLC RT=4.98 min, method A).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate solvent was removed in vacuo
  3. customThe residue was partitioned between CH2Cl2 and aqueous NaHCO3
  4. customThe organic phase was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d5e747c3b1e5473395e817ac03270e05
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

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