Trifluoroacetic acid → (R)-5-[3-(trifluoromethyl)phenyl]pyrrolidin-2-one

HRID 1972238Notes

Reaction equation

HRID 1972238 reaction equation
C(OC([N:8]1[C@@H:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[CH2:11][CH:10](C(O)=O)[C:9]1=[O:26])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:22][C:19]([F:20])([F:21])[C:15]1[CH:14]=[C:13]([C@@H:12]2[NH:8][C:9](=[O:26])[CH2:10][CH2:11]2)[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59485976(5R)-1-(tert-butoxycarbonyl)-5-[3-(trifluoromethyl)phenyl]-2-oxopyrrolidine-3-carboxylic acid

Product 1

HCID 59485901(R)-5-[3-(trifluoromethyl)phenyl]pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The mixture of (5R)-1-(tert-butoxycarbonyl)-5-[3-(trifluoromethyl)phenyl]-2-oxopyrrolidine-3-carboxylic acid obtained in Step E (ca. 1.21 mmol) and 30% TFA in DCM (6 mL) is stirred at rt for 30 min. The reaction mixture is then dissolved in DCM (120 mL), washed with saturated aq. NaHCO3 (40 mL) and brine (40 mL) and dried over Na2SO4. Concentration to give (R)-5-[3-(trifluoromethyl)phenyl]pyrrolidin-2-one as a slight brown solid (278 mg, 100% overall yield for two steps). This product is used for the next step without further purification. HPLC-MS calculated for C11H10F3NO (M+H+) 230.07, found 230.00.

Workup

  1. washwashed with saturated aq. NaHCO3 (40 mL) and brine (40 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationConcentration
  4. customto give

Sources & evidence

ORD record
ord-09a7e11bf02f416eb21a6f6d2c2415cc
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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