Hydrochloric Acid → 5-Oxo-2-pyrrolidinepropanoic acid o-chlorobenzyl ester

HRID 2290531Notes

Reaction equation

HRID 2290531 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.[Cl:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][OH:16]>C(OCC)C>[Cl:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][O:16][C:5](=[O:9])[CH2:6][CH2:7][CH:8]1[CH2:1][CH2:2][C:3](=[O:10])[NH:4]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 288102-Chlorobenzyl alcoholHCID 71893Rolziracetam

Product 1

HCID 155888725-Oxo-2-pyrrolidinepropanoic acid o-chlorobenzyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

Five grams of dihydro-1H-pyrrolizine-3,5(2H,6H)-dione (III) are dissolved in 31 g of o-chlorobenzyl alcohol and 0.2 ml of concentrated hydrochloric acid is added. The solution is heated at 100° C. for 71 hours. The mixture is cooled and dissolved in 150 ml of anhydrous diethylether. The solution is cooled to induce crystallization and the resulting crystals are isolated by filtration. Recrystallization from toluene-diethyl ether yields 5-oxo-2-pyrrolidinepropanoic acid o-chlorobenzyl ester with a melting point of 99°-100° C.

Workup

  1. temperatureThe mixture is cooled
  2. temperatureThe solution is cooled
  3. customcrystallization
  4. customthe resulting crystals are isolated by filtration
  5. customRecrystallization from toluene-diethyl ether

Sources & evidence

ORD record
ord-399f93f53c6c4c93a9269ffcd453ddc3
Source dataset
uspto-grants-1986_10
Patent number
US04617310

Reaction notes

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