Ethanol → 1-(4-Isopropyl-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid ethyl ester

HRID 889026Notes

Reaction equation

HRID 889026 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

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 31510031-(4-Isopropylphenyl)-5-oxopyrrolidine-3-carboxylic acid

Product 1

HCID 508737211-(4-Isopropyl-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid ethyl esterYield 100%

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%).

Workup

  1. temperatureThe mixture was cooled
  2. customsolvent was removed
  3. dissolutionThe residue was dissolved in ethyl acetate (20 ml)
  4. washThe organic layer was washed with saturated NaHCO3 and saturated brine solution (20 ml)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-549c075cf75a45dc8520e3b5311bd618
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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