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

HRID 2290533Notes

Reaction equation

HRID 2290533 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][C:16]([CH2:17][OH:18])=[CH:15][CH:14]=1>>[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][O:18][C:5](=[O:9])[CH2:6][CH2:7][CH:8]2[CH2:1][CH2:2][C:3](=[O:10])[NH:4]2)=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 133974-Chlorobenzyl alcoholHCID 71893Rolziracetam

Product 1

HCID 155888745-Oxo-2-pyrrolidinepropanoic acid p-chlorobenzyl ester

Conditions

Temperature
100 °C

Procedure

Five grams of dihydro-1H-pyrrolizine-3,5(2H,6H) -dione (III) are dissolved in 31 g of p-chlorobenzyl alcohol and 0.2 ml of concentrated hydrochloric acid is added. The solution is heated at 100° C. for 65 hours. The mixture is cooled and chromatographed over silica gel in dichloromethane. The starting p-chlorobenzyl alcohol is eluted with dichloromethane and the product is eluted with 2.5% methanol in dichloromethane. The eluate containing the product is concentrated at reduce pressure and the residual oil solidifies upon standing. The solid is recrystallized from toluene diethyl ether to yield 5-oxo-2-pyrrolidinepropanoic acid p-chlorobenzyl ester with a melting point of 63°-64° C.

Workup

  1. temperatureThe mixture is cooled
  2. customchromatographed over silica gel in dichloromethane
  3. washThe starting p-chlorobenzyl alcohol is eluted with dichloromethane
  4. washthe product is eluted with 2.5% methanol in dichloromethane
  5. additionThe eluate containing the product
  6. concentrationis concentrated
  7. customThe solid is recrystallized from toluene diethyl ether

Sources & evidence

ORD record
ord-3f0cdd29d5254e8dbb1322ff44f81685
Source dataset
uspto-grants-1986_10
Patent number
US04617310

Reaction notes

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