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

HRID 638000Notes

Reaction equation

HRID 638000 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][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][OH:18])=[CH:15][CH:14]=1>>[CH3:12][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 115054-Methylbenzyl alcoholHCID 71893Rolziracetam

Product 1

HCID 155888765-Oxo-2-pyrrolidinepropanoic acid p-methylbenzyl ester

Conditions

Temperature
100 °C

Procedure

Five grams of dihydro-1H-pyrrolizine-3,5(2H,6H)-dione (III) are dissolved in 27 g of p-methylbenzyl alcohol and 0.2 ml of concentrated hydrochloric acid is added. The solution is heated at 100° C. for 48 hours. The mixture is cooled and chromatographed over silica gel in dichloromethane. The starting p-methylbenzyl alcohol is eluted with dichloromethane and the product is eluted with 1.0% methanol in dichloromethane. The eluate containing the product is concentrated at reduced pressure and the residual oil solidifies upon standing. The solid is recrystallized from toluene-diethyl ether to yield 5-oxo-2-pyrrolidinepropanoic acid p-methylbenzyl ester with a melting point of 71°-72° C.

Workup

  1. temperatureThe mixture is cooled
  2. customchromatographed over silica gel in dichloromethane
  3. washThe starting p-methylbenzyl alcohol is eluted with dichloromethane
  4. washthe product is eluted with 1.0% methanol in dichloromethane
  5. additionThe eluate containing the product
  6. concentrationis concentrated at reduced pressure
  7. customThe solid is recrystallized from toluene-diethyl ether

Sources & evidence

ORD record
ord-46af0e158f02413b979b20e2c310f0b2
Source dataset
uspto-grants-1985_12
Patent number
US04559358

Reaction notes

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