Trifluoroacetic acid → 3-(4-Trifluoromethyl-phenyl)-2,5-dihydro-1H-pyrrole
Reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2(O)[CH2:13][CH2:12][NH:11][CH2:10]2)=[CH:5][CH:4]=1.C(O)(C(F)(F)F)=O>ClCCl>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH2:10][NH:11][CH2:12][CH:13]=2)=[CH:7][CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of 0.43 mmol rac-3-(4-Trifluoromethyl-phenyl)-pyrrolidin-3-ol in 0.4 ml dichloromethane under argon, was added 0.4 ml TFA. The reaction mixture was stirred at reflux for 5 days and concentrated. The residue was dissolved in ethyl acetate and NaOH 2N was added until pH 9-10. The organic phases were dried over Na2SO4 and evaporated to yield the title compound (18%) as an oil MS (m/e): 214.2 ([M+1], 100%).