Toluene → Ethyl trans-4-(p-fluorophenyl)-6-oxo-3-piperidinecarboxylate

HRID 1357337Notes

Reaction equation

HRID 1357337 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][CH2:10][CH:9]2[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.C[O-].[Na+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[CH2:13][C:12](=[O:14])[NH:11][CH2:10][C@H:9]2[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 10942334Sodium MethoxideHCID 111400223-Ethoxycarbonyl-4-(4'-fluorophenyl)piperidin-6-one

Product 1

HCID 11161405Ethyl trans-4-(p-fluorophenyl)-6-oxo-3-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

3.8 g of the cis/trans mixture of ethyl 4-(p-fluorophenyl)-6-oxo-3-piperidinecarboxylate obtained in Examples 4 to 6 was added to 100 mL of toluene, and 2.7 mL of a 28% methanol solution of sodium methoxide was added. The reaction mixture was heated at 110° C. for 2.5 hours, then poured into ice water and extracted with ethyl acetate. The extract was washed with water, dried and concentrated to obtain 3.28 g of ethyl trans-4-(p-fluorophenyl)-6-oxo-3-piperidinecarboxylate.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d158860669334f0aba9128a17e90fbbd
Source dataset
uspto-grants-2003_07
Patent number
US06590102B1

Reaction notes

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