Ammonia → (3-(3,4-Dichlorophenyl)-5-oxopyrrolidin-3-yl)acetic acid ethyl ester

HRID 323198Notes

Reaction equation

HRID 323198 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]([C:21]#[N:22])([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=1)[CH2:7][C:8](OCC)=[O:9])[CH3:2].N.C(OCC)(=O)C>C(O)C>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:7][C:8](=[O:9])[NH:22][CH2:21]1)[CH3:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 54083037Diethyl 3-cyano-3-(3,4-dichlorophenyl)pentanedioate

Product 1

HCID 54080079(3-(3,4-Dichlorophenyl)-5-oxopyrrolidin-3-yl)acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Combine Raney nickel (twice washed with water and twice washed with ethanol, 3.6 kg), 3-cyano-3-(3,4-dichlorophenyl)pentanedioic acid diethyl ester (1260 g, 3.51 mol), ethanol (9 L), and an aqueous concentrated ammonia solution (1.6 L) in a 5 gallon autoclave. Hydrogenate at 55 psi. After 20 hours, vent the vessel, purge with nitrogen, and filter. Rinse the solids with ethanol (about 1 L). Evaporate the filtrate in vacuo to give a residue. Combine the residue and ethyl acetate (10 L) and extract twice with water (1 L) and then with brine. Dry the organic layer over MgSO4, filter, and concentrate in vacuo to give a residue. Crystallize the residue from ethyl acetate (about 1.8 L) and heptane (about 7.2 L) to give a solid. Collect the solid to give the title compound: mp; 98-99° C.

Workup

  1. washCombine Raney nickel (twice washed with water
  2. custompurge with nitrogen
  3. filtrationfilter
  4. washRinse the solids with ethanol (about 1 L)
  5. customEvaporate the filtrate in vacuo
  6. customto give a residue
  7. extractionextract twice with water (1 L)
  8. dry with materialDry the organic layer over MgSO4
  9. filtrationfilter
  10. concentrationconcentrate in vacuo
  11. customto give a residue
  12. customCrystallize the residue from ethyl acetate (about 1.8 L) and heptane (about 7.2 L)
  13. customto give a solid
  14. customCollect the solid

Sources & evidence

ORD record
ord-06056266c1004b529f24391728073599
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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