Hydrochloric Acid → HCID 14811461, compound

HRID 892610Notes

Reaction equation

HRID 892610 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][NH:3]1.[Li]CCCC.C1COCC1.[C:17]1(=[O:23])[O:22][C:20](=[O:21])[CH2:19][CH2:18]1.Cl>C1COCC1>[O:23]=[C:17]([N:3]1[CH2:4][CH2:5][CH2:6][C:2]1=[O:1])[CH2:18][CH2:19][C:20]([OH:22])=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7922Succinic anhydrideHCID 120252-PyrrolidoneHCID 178420697HCID 178420697, compound

Product 1

HCID 14811461HCID 14811461, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

A solution of 2-oxopyrrolidine (5.00 g) in THF (60 ml) was cooled to -50° C., and a 1.55 M n-BuLi/THF solution (38 ml) was dropwise added thereto. After 0.5 hour's stirring at -30° C., succinic anhydride (6.00 g) was added dropwise, followed by stirring at a temperature of -30°--20° C. for 0.5 hour. The reaction mixture was poured into ice water and adjusted to pH 4 with 1N hydrochloric acid, and extracted with n-butanol. The organic layer was washed with saturated brine and concentrated to give 9.42 g of 4-oxo-4-(2-oxo-1-pyrrolidinyl)butyric acid.

Workup

  1. stirringby stirring at a temperature of -30°--20° C. for 0.5 hour
  2. extractionextracted with n-butanol
  3. washThe organic layer was washed with saturated brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e2c53c4e4560415b87f66a7b4bb63786
Source dataset
uspto-grants-1992_06
Patent number
US05118811

Reaction notes

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