Diethyl 2-cyano-3-(p-fluorophenyl)glutarate → Ethyl trans-4-(p-fluorophenyl)-6-oxo-3-piperidinecarboxylate

HRID 1531352Notes

Reaction equation

HRID 1531352 reaction equation
[C:1]([CH:3]([CH:9]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[CH2:10][C:11](OCC)=[O:12])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[H][H]>[Ni].C(O)C>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C@@H:9]2[CH2:10][C:11](=[O:12])[NH:2][CH2:1][C@H:3]2[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 10935698Diethyl 2-cyano-3-(p-fluorophenyl)glutarateHCID 178418361HCID 178418361, compound

Product 1

HCID 11161405Ethyl trans-4-(p-fluorophenyl)-6-oxo-3-piperidinecarboxylateYield 46.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

5 g of diethyl 2-cyano-3-(p-fluorophenyl)glutarate obtained in Examples 1 to 3 was added to a mixture of 1.4 g of a commercially available developed Raney nickel and 120 mL of ethanol, and the reaction mixture was allowed to react at 27° C. for 6 hours under a hydrogen pressure of 2.5 atm (gauge pressure) of hydrogen. The reaction mixture was filtered through Celite, and the filtrate was concentrated. The resulting oily substance was recrystallized to obtain 2 g of ethyl trans-4-(p-fluorophenyl)-6-oxo-3-piperidinecarboxylate as a crystalline white powder.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customThe resulting oily substance was recrystallized

Sources & evidence

ORD record
ord-88cdf4c127224585b6c28cef0be7f266
Source dataset
uspto-grants-2001_03
Patent number
US06197960B1

Reaction notes

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