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

HRID 1436892Notes

Reaction equation

HRID 1436892 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>C(O)(=O)C.[Zn]>[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

In 4600 ml of acetic acid was dissolved 190 g of 1-benzyloxycarbonyl-2-(4-fluoro-2-methylphenyl)-4-oxo-3,4-dihydro-2H-pyridine, and added thereto was 91 g of zinc powder and the mixture was stirred at room temperature for 24 hours. From the reaction mixture was removed insoluble matters by filtration, and the solvent was removed by distillation under reduced pressure. 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, and dried over magnesium sulfate. The solvent was removed by distillation under reduced pressure, and 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 as shown in Table 125 below.

Workup

  1. additionadded
  2. customFrom the reaction mixture was removed insoluble matters
  3. filtrationby filtration
  4. customthe solvent was removed by distillation under reduced pressure
  5. additionTo the residue was added 400 ml of ethyl acetate
  6. washthe mixture was washed with an aqueous sodium hydrogen carbonate solution and saturated brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed by distillation under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1)

Sources & evidence

ORD record
ord-3a96cfa197484558b5f04da20ba6d265
Source dataset
uspto-grants-2009_11
Patent number
US07619092B2

Reaction notes

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