Benzyl 2-(4-fluoro-2-methylphenyl)-4-oxo-3,4-dihydropyridine-1(2H)-carboxylate → HCID 21927685, compound

HRID 133491Notes

Reaction equation

HRID 133491 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH:16]=[CH:15][C:14](=[O:17])[CH2:13][CH:12]1[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[CH3:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Zn].C(O)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH:12]1[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[CH3:25])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 21927686Benzyl 2-(4-fluoro-2-methylphenyl)-4-oxo-3,4-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 21927685HCID 21927685, compoundYield 86.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To 4600 ml of an acetic acid solution containing 190 g of 1-benzyloxycarbonyl-2-(4-fluoro-2-methylphenyl)-4-oxo-2,3-dihydro-1H-pyridine was added 91 g of zinc powder, and the mixture was stirred at room temperature for 24 hours. Insoluble materials were filtered off from the reaction solution, and the filtrate was concentrated. To the residue was added 400 ml of ethyl acetate, and the mixture was washed with an aqueous sodium hydrogen carbonate solution and saturated brine, dried and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1) to give 166 g of 1-benzyloxycarbonyl-2-(4-fluoro-2-methylphenyl)-4-oxopiperidine.

Workup

  1. filtrationInsoluble materials were filtered off from the reaction solution
  2. concentrationthe filtrate was concentrated
  3. additionTo the residue was added 400 ml of ethyl acetate
  4. washthe mixture was washed with an aqueous sodium hydrogen carbonate solution and saturated brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1)

Sources & evidence

ORD record
ord-8fee01048f2d40848b875f4cec8d6b6f
Source dataset
uspto-grants-2008_06
Patent number
US07390905B2

Reaction notes

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