Hydrochloric Acid → HCID 558769, compound

HRID 1262685Notes

Reaction equation

HRID 1262685 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 is 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 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 of anhydrous diethylether, 1 g of activated charcoal
  6. additionis 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-00b8a5375a9c47829e6cc1c305af74a6
Source dataset
uspto-grants-1984_06
Patent number
US04452990

Reaction notes

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