Hydrochloric Acid → HCID 23324912, compound

HRID 1380950Notes

Reaction equation

HRID 1380950 reaction equation
C[O:2][C:3](=[O:18])[CH2:4][CH2:5][CH:6]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][C:8](=[O:17])[NH:7]1.C[O:20][C:21](=[O:36])[CH2:22][CH:23]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH:24]1[CH2:28][CH2:27][C:26](=[O:29])[NH:25]1.Cl>[OH-].[Na+]>[O:29]=[C:26]1[NH:25][CH:24]([CH:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:22][C:21]([OH:36])=[O:20])[CH2:28][CH2:27]1.[O:17]=[C:8]1[NH:7][CH:6]([CH2:5][CH2:4][C:3]([OH:18])=[O:2])[CH:10]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:9]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 13534114HCID 13534114, compoundHCID 13534115HCID 13534115, compound

Product 2

HCID 23324912HCID 23324912, compoundHCID 23324927HCID 23324927, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 93.4 g of 5-oxo-3-phenyl-2-pyrrolidinepropanoic acid methyl ester and 5-oxo-βphenyl-2-pyrrolidinepropanoic acid methyl ester in 370 ml of 1N aqueous sodium hydroxide solution is heated to 60° C. for four hours. Excess aqueous hydrochloric acid (1 N, 370 ml) is added and the solution is concentrated under reduced pressure to yield 5-oxo-β-phenyl-2-pyrrolidinepropanoic acid and 5-oxo-3-phenyl-2-pyrrolidinepropanoic acid. The acids are dissolved in 300 ml of acetic anyhydride and the solution heated to 90° C. The solution is filtered hot and the filtrate concentrated in vacuo. The oil is chromatographed on silica gel (200-400 mesh) to give cis- and trans-dihydro-1-phenyl-1H-pyrrolizine-3,5(2H,6H)-diones as a white solid with mp 151°-3° C.

Workup

  1. concentrationthe solution is concentrated under reduced pressure

Sources & evidence

ORD record
ord-db096dc6b7084e9f95192b607cfef74c
Source dataset
uspto-grants-1986_04
Patent number
US04584313

Reaction notes

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