Ethanol → 2-Oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester

HRID 889032Notes

Reaction equation

HRID 889032 reaction equation
[O:1]=[C:2]1[CH:6]([C:7]([OH:9])=[O:8])[CH2:5][CH2:4][N:3]1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=1.S(Cl)(Cl)=O.[CH2:24](O)[CH3:25]>>[CH2:24]([O:8][C:7]([CH:6]1[CH2:5][CH2:4][N:3]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:17])([F:19])[F:18])[CH:11]=2)[C:2]1=[O:1])=[O:9])[CH3:25]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 155160613-Carboxy-1-(3-trifluoromethylphenyl)-2-pyrrolidinone

Product 1

HCID 574296622-Oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidine-3-carboxylic acid ethyl esterYield 65%

Conditions

Temperature
57.5 °C

Procedure

A mixture of 2-oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidine-3-carboxylic acid obtained in step 1 (0.7 g, 2.56 mmol), thionyl chloride (0.36 g, 3.0 mmol), and ethanol (10 ml) were 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 sat. NaHCO3 and saturated brine solution, dried over Na2SO4 and evaporated to obtain 2-oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester as a yellow oil (0.5 g, 65%).

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 sat. NaHCO3 and saturated brine solution
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-a4d62c33da8d4e57b8c903206c3c64df
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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