Hydrochloric Acid → HCID 558769, compound

HRID 637995Notes

Reaction equation

HRID 637995 reaction equation
[CH2:1]1[CH:8]2[N:4]([C:5](=[O:9])[CH2:6][CH2:7]2)[C:3](=[O:10])[CH2:2]1.Cl.[CH3:12][OH:13]>>[CH3:12][O:13][C:5](=[O:9])[CH2:6][CH2:7][CH:8]1[CH2:1][CH2:2][C:3](=[O:10])[NH:4]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 71893Rolziracetam

Product 1

HCID 558769HCID 558769, compound

Procedure

Twenty-eight grams of dihydro-1H-pyrrolizine-3,5(2H,6H)-dione (III) are dissolved in 100 g of methyl alcohol and 0.2 ml of concentrated hydrochloric acid is added. The solution is heated at reflux for 104 hours. The mixture is cooled and excess methyl alcohol is distilled at reduced pressure. The residual oil is dissolved in 1 l of anhydrous diethylether, 1 g of activated charcoal is added and the resulting suspension is filtered through filter aid. The filtrate is concentrated at reduced pressure and the resulting crystals are isolated by filtration. Recrystallization from methanol yields 5-oxo-2-pyrrolidinepropanoic acid methyl ester with a melting point of 52°-53° C.

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux for 104 hours
  3. temperatureThe mixture is cooled
  4. distillationexcess methyl alcohol is distilled at reduced pressure
  5. dissolutionThe residual oil is dissolved in 1 l of anhydrous diethylether
  6. addition1 g of activated charcoal is added
  7. filtrationthe resulting suspension is filtered
  8. filtrationthrough filter aid
  9. concentrationThe filtrate is concentrated at reduced pressure
  10. customthe resulting crystals are isolated by filtration
  11. customRecrystallization from methanol

Sources & evidence

ORD record
ord-b4ee7229141142948bbf290910fea0bb
Source dataset
uspto-grants-1985_12
Patent number
US04559358

Reaction notes

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