Hydrochloric Acid → Ethyl 3-(5-oxopyrrolidin-2-yl)propanoate

HRID 637996

Reaction equation

HRID 637996 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.[CH2:12]([OH:14])[CH3:13]>>[CH2:12]([O:14][C:5](=[O:9])[CH2:6][CH2:7][CH:8]1[CH2:1][CH2:2][C:3](=[O:10])[NH:4]1)[CH3:13]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 71893Rolziracetam

Product 1

HCID 558761Ethyl 3-(5-oxopyrrolidin-2-yl)propanoate

Procedure

Twenty-eight grams of dihydro-1H-pyrrolizine-3,5(2H,6H)-dione (III) are dissolved in 100 g of ethyl 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 ethyl alcohol is distilled at reduced pressure. The 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 carbon tetrachloride-petroleum ether yields 5-oxo-2-pyrrolidinepropanoic acid ethyl ester with a melting point of 60°-61° C.

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux for 104 hours
  3. temperatureThe mixture is cooled
  4. distillationexcess ethyl alcohol is distilled at reduced pressure
  5. dissolutionThe 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 carbon tetrachloride-petroleum ether

Sources & evidence

ORD record
ord-52a7372cf6ee4c6ebaa0acf258279316
Source dataset
uspto-grants-1985_12
Patent number
US04559358

Linked notes

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