Ammonia → 3-Ethyl-2-oxopyrrolidine-3-carbonitrile

HRID 714779Notes

Reaction equation

HRID 714779 reaction equation
[CH2:1]([C:3]1([C:18]#[N:19])[CH2:7][CH2:6][N:5](C(=O)C2C=CC(F)=CC=2)[C:4]1=[O:17])[CH3:2].N>C(O)C.C(OC(C)C)(C)C>[CH2:1]([C:3]1([C:18]#[N:19])[CH2:7][CH2:6][NH:5][C:4]1=[O:17])[CH3:2]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 1178403873-Ethyl-1-(4-fluorobenzoyl)-2-oxopyrrolidine-3-carbonitrile

Product 1

HCID 553002093-Ethyl-2-oxopyrrolidine-3-carbonitrileYield 14%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7914Diisopropyl EtherSolvent

Procedure

To a solution of 3-ethyl-1-(4-fluorobenzoyl)-2-oxopyrrolidine-3-carbonitrile (1.1 g) obtained in Step G in ethanol (15 mL) was added dropwise 28% aqueous ammonia solution (5 mL), and the mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate). The obtained crude crystals were dissolved in diisopropyl ether, and the remaining solid was removed by filtration. The solvent was evaporated under reduced pressure, and the resulting solid was collected by filtration, and washed with diisopropyl ether to give the title compound (82 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
  3. customThe obtained crude crystals
  4. customthe remaining solid was removed by filtration
  5. customThe solvent was evaporated under reduced pressure
  6. filtrationthe resulting solid was collected by filtration
  7. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-2ec0856fdce54fd0baba347a0eb505f0
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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