Hydrochloric Acid → HCID 23324911, compound

HRID 464739Notes

Reaction equation

HRID 464739 reaction equation
C[O:2][C:3](=[O:20])[CH2:4][CH2:5][CH:6]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH2:9][C:8](=[O:19])[NH:7]1.C[O:22][C:23](=[O:40])[CH2:24][CH:25]([C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=1)[CH:26]1[CH2:30][CH2:29][C:28](=[O:31])[NH:27]1.Cl>[OH-].[Na+]>[CH3:39][O:38][C:35]1[CH:34]=[CH:33][C:32]([CH:25]([CH:26]2[CH2:30][CH2:29][C:28](=[O:31])[NH:27]2)[CH2:24][C:23]([OH:40])=[O:22])=[CH:37][CH:36]=1.[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([CH:10]2[CH2:9][C:8](=[O:19])[NH:7][CH:6]2[CH2:5][CH2:4][C:3]([OH:20])=[O:2])=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 53888741HCID 53888741, compoundHCID 54515331HCID 54515331, compound

Product 2

HCID 23324911HCID 23324911, compoundHCID 23324923HCID 23324923, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 132.3 g of 3-(4-methoxyphenyl)-5-oxo-2-pyrrolidinepropanoic acid methyl ester and β-(4-methoxyphenyl)-5-oxo-2-pyrrolidinepropanoic acid methyl ester in 480 ml of 1 N aqueous sodium hydroxide solution is heated to 60° C. for four hours. Excess aqueous hydrochloric acid (3 N, 170 ml) is added and the solution concentrated under reduced pressure to give β-(4-methoxyphenyl)-5-oxo-2-pyrrolidinepropanoic acid and 3-(4-methoxyphenyl)-5-oxo-2-pyrrolidinepropanoic acid. The acids are dissolved in 300 ml of acetic anhydride, and the solution is heated to 90° C. The solution is filtered hot and the filtrate concentrated in vacuo. The oil is dissolved in chloroform, treated with activated carbon, filtered and concentrated. The oil is chromatographed on silica gel (200-400 mesh) (elution with chloroform) to give cis-and trans-dihydro-1-(4-methoxyphenyl)-1H-pyrrolizine-3,5(2H,6H)-dione as a white solid with a mp 125°-127° C.

Workup

  1. concentrationthe solution concentrated under reduced pressure

Sources & evidence

ORD record
ord-f90b684cae314adebf76d1f8b7118730
Source dataset
uspto-grants-1985_10
Patent number
US04548947

Reaction notes

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