Ethanol → 1-(4-Isopropyl-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid ethyl ester
Reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=[O:15])[CH2:13][CH:12]([C:16]([OH:18])=[O:17])[CH2:11]2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].S(Cl)(Cl)=O.[CH2:23](O)[CH3:24]>>[CH2:23]([O:17][C:16]([CH:12]1[CH2:13][C:14](=[O:15])[N:10]([C:7]2[CH:6]=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=2)[CH2:11]1)=[O:18])[CH3:24]Participants
4
Conditions
- Temperature
- 57.5 °C
Procedure
A mixture of 1-(4-isopropyl-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid obtained in step 1 (0.6 g, 2.42 mmol), thionyl chloride (0.35 g, 2.90 mmol), and ethanol (10 ml) was heated at 55-60° C. for 2 hours. The mixture was cooled and solvent was removed. The residue was dissolved in ethyl acetate (20 ml). The organic layer was washed with saturated NaHCO3 and saturated brine solution (20 ml). The organic layer was dried over Na2SO4 and evaporated to obtain 1-(4-isopropyl-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid ethyl ester as yellow oil (0.7 g, 100%).