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

HRID 323195Notes

Reaction equation

HRID 323195 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].C(O)C.N>[Ni].CO.ClCCl>[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

6

Reactant 3

HCID 222AmmoniaHCID 702EthanolHCID 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 2

HCID 935NickelCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

Combine 3-cyano-3-(3,4-dichlorophenyl)pentanedioic acid diethyl ester (32 g, 89 mmol) and ethanol (150 mL) in a Parr bottle. Add Raney nickel (100 g) and an aqueous concentrated ammonia solution (40 mL). Hydrogenate at 50 psi for 24 h. Filter through a celite pad and rinse the solids with ethanol. Evaporate the filtrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 6% methanol/dichloromethane to give the title compound: Rf=0.34 (silica gel, 6% methanol/dichloromethane); mp; 87-90° C. Elemental Analysis calculated for C14H15Cl2NO3: C 53.18; H 4.78; N 4.43; Found: C 53.34; H 4.71; N 4.51.

Workup

  1. filtrationFilter through a celite pad
  2. washrinse the solids with ethanol
  3. customEvaporate the filtrate in vacuo
  4. customto obtain a residue

Sources & evidence

ORD record
ord-4f71013ac1fb4b8b9d5731e2b54d5306
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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