3,3-Diphenyl-2-pyrrolidinone → 3,3-Diphenyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}pyrrolidin-2-one

HRID 1667191Notes

Reaction equation

HRID 1667191 reaction equation
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][CH2:10][NH:9][C:8]2=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[F:25][C:26]([F:38])([F:37])[C:27]1[CH:28]=[C:29]([S:33](Cl)(=[O:35])=[O:34])[CH:30]=[CH:31][CH:32]=1>O1CCCC1>[C:13]1([C:7]2([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:11][CH2:10][N:9]([S:33]([C:29]3[CH:30]=[CH:31][CH:32]=[C:27]([C:26]([F:25])([F:37])[F:38])[CH:28]=3)(=[O:35])=[O:34])[C:8]2=[O:12])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 2382533,3-Diphenyl-2-pyrrolidinoneHCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 452750473,3-Diphenyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,3-diphenylpyrrolidin-2-one (Example 1A, 0.237 g, 1.0 mmol) dissolved in tetrahydrofuran (10 mL) was added potassium t-butoxide (1.0 M in tetrahydrofuran, 1.5 mL, 1.5 mmol) under nitrogen. The reaction mixture was stirred for 15 minutes, and then 3-(trifluoromethyl)benzene-1-sulfonyl chloride (0.294 g, 1.2 mmol) was added. The reaction mixture was stirred for 4 hours at room temperature. The reaction mixture was concentrated and then diluted with ethyl acetate and water. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography (Analogix®, Burlington, Wis.) eluting with ethyl acetate/hexane (40:60) gave the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.26-8.12 (m, 3H), 7.87 (t, J=7.8, 1H), 7.28-7.16 (m, 6H), 7.08-6.98 (m, 4H), 3.82 (t, J=6.4, 2H), 2.90 (t, J=6.4, 2H); MS (DCI) m/z 446.0 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred for 4 hours at room temperature
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with ethyl acetate and water
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washSilica gel chromatography (Analogix®, Burlington, Wis.) eluting with ethyl acetate/hexane (40:60)

Sources & evidence

ORD record
ord-717e94499f8f48c8b4c9be48241c40fb
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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