Acetic Acid → HCID 70023596, compound

HRID 398397Notes

Reaction equation

HRID 398397 reaction equation
C([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C@H:10]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:9]1)C1C=CC=CC=1.C(O)(=O)C>C(O)C.[Pd]>[CH2:22]([O:21][C:19]([C@H:10]1[C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:12][NH:8][CH2:9]1)=[O:20])[CH3:23]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 70024099HCID 70024099, compound

Product 1

HCID 70023596HCID 70023596, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-benzyl-trans-3-ethoxycarbonyl-4-(2-pyridyl)pyrrolidine from step 2 above (5.0 g, 16 mmol) and 10% Pd on carbon (750 mg) in ethanol (30 mL) containing acetic acid (3 mL) was shaken under an atmosphere of hydrogen (40 psi) on a Parr apparatus at ambient temperature for 18 h. The catalyst was removed by filtration and the filtrate solvents were removed in vacuo. The residue was partitioned between CH2Cl2 and aqueous NaHCO3. The organic phase was separated, dried over MgSO4, filtered, and concentrated in vacuo to give the title compound as an oil (3.3 g; HPLC RT=2.43 min, method A).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate solvents were 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. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-22366045eede442a8928dcbae4c084d6
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

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