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

HRID 1531353Notes

Reaction equation

HRID 1531353 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.[O-]CC.[Na+]>C1(C)C=CC=CC=1>[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

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 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 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

0.1 g of the cis/trans mixture of ethyl 4-(p-fluorophenyl)-6-oxo-3-piperidinecarboxylate obtained in Examples 4 to 6 was added to 10 mL of toluene, and 26 mg of sodium ethoxide was added. The reaction mixture was heated at 90° C. for 5 hours, then poured into ice water, and extracted with ethyl acetate. The extract was washed with water, dried and concentrated to obtain 50 mg 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-62c9bb57808c431fb7521a9d45d29653
Source dataset
uspto-grants-2001_03
Patent number
US06197960B1

Reaction notes

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