Water → (5R)-5-[4'-(Trifluoromethoxy)-1,1'-biphenyl-4-yl]-2-pyrrolidinone

HRID 28337Notes

Reaction equation

HRID 28337 reaction equation
C([N:4]1[C@@H:8]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:7][CH2:6][C:5]1=[O:26])C=C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1COCC1.O>C([O-])(O)=O.[Na+].C(OCC)(=O)C>[F:25][C:22]([F:23])([F:24])[O:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[CH:13]=[CH:14][C:9]([C@@H:8]3[NH:4][C:5](=[O:26])[CH2:6][CH2:7]3)=[CH:10][CH:11]=2)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 521998p-Toluenesulfonic acid monohydrateHCID 68929317(5R)-1-Allyl-5-[4'-(trifluoromethoxy)-1,1'-biphenyl-4-yl]-2-pyrrolidinone

Product 1

HCID 59787796(5R)-5-[4'-(Trifluoromethoxy)-1,1'-biphenyl-4-yl]-2-pyrrolidinone

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Under argon, (5R)-1-allyl-5-[4′-(trifluoromethoxy)-1,1′-biphenyl-4-yl]-2-pyrrolidinone (XVII-1) (0.41 g, 1.14 mmol) is initially charged in a Schlenk tube together with Pd[PPh3]4 (131.7 mg, 0.114 mmol) and p-toluenesulphonic acid hydrate (0.52 g, 2.74 mmol), and THF (2 ml, degassed) and 1 ml of H2O are added. The yellow suspension is heated under reflux for 3 h. For work-up, the mixture, which was cooled to room temperature, is diluted with NaHCO3 solution and admixed with ethyl acetate and filtered through kieselguhr. The combined organic phases are dried (Na2SO4) and concentrated under reduced pressure.

Workup

  1. additionare added
  2. temperatureThe yellow suspension is heated
  3. temperatureunder reflux for 3 h
  4. filtrationfiltered through kieselguhr
  5. dry with materialThe combined organic phases are dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-800e8880e9c6483388b654c5caecdc1a
Source dataset
uspto-grants-2008_09
Patent number
US07419936B2

Reaction notes

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