Trifluoroacetic acid → 3-(4-Trifluoromethyl-phenyl)-2,5-dihydro-1H-pyrrole

HRID 552679Notes

Reaction equation

HRID 552679 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]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 1208963-(4-(Trifluoromethyl)phenyl)pyrrolidin-3-ol

Product 1

HCID 590304773-(4-Trifluoromethyl-phenyl)-2,5-dihydro-1H-pyrroleYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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%).

Workup

  1. temperatureat reflux for 5 days
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. additionNaOH 2N was added until pH 9-10
  5. dry with materialThe organic phases were dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-62bb67eed92d497d9672300223e300d4
Source dataset
uspto-grants-2011_05
Patent number
US07951836B2

Reaction notes

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