5-(4-Fluorophenyl)pyrrolidin-2-one → HCID 18182761, compound

HRID 1359127Notes

Reaction equation

HRID 1359127 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[NH:12][C:11](=[O:13])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:14](OC([O-])=O)(=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17]>C1(C)C=CC=CC=1>[C:16]([O:15][C:14]([N:12]1[CH:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:9][CH2:10][C:11]1=[O:13])=[O:20])([CH3:19])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 132933735-(4-Fluorophenyl)pyrrolidin-2-oneHCID 22064466Tert-butyldicarbonate

Product 1

HCID 18182761HCID 18182761, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

22.6 g (0.126 mol) of 5-(4-fluorophenyl)-pyrrolidin-2-one in 200 ml of toluene are boiled at reflux with 55 g (0.25 mol) of tert-butyl pyrocarbonate for 5 hours. After cooling the mixture, is washed repeatedly with water and the organic phase, is dried and concentrated under reduced pressure using a rotary evaporator. The residue is stirred with petroleum ether and the crystals are filtered off with suction. This gives 21.8 g (62% yield of theory) of 1-(tert-butyloxycarbonyl)-5-(4-fluorophenyl)-pyrrolidin-2-one of m.p. 117°.

Workup

  1. temperatureAfter cooling the mixture
  2. washis washed repeatedly with water
  3. customthe organic phase, is dried
  4. concentrationconcentrated under reduced pressure
  5. customa rotary evaporator
  6. filtrationthe crystals are filtered off with suction

Sources & evidence

ORD record
ord-a7eadfcb1921459986b4e8d8b2237e76
Source dataset
uspto-grants-2003_07
Patent number
US06599924B1

Reaction notes

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