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

HRID 1262687Notes

Reaction equation

HRID 1262687 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 is 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-c33afdcc81c34fba8c55d3f68f35e098
Source dataset
uspto-grants-1984_06
Patent number
US04452990

Reaction notes

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