3,3-Diphenyl-2-pyrrolidinone → HCID 67443366, compound

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Reaction Steps

To 3,3-diphenylpyrrolidin-2-one (166 mg, 0.7 mmol; Example 1A) in anhydrous tetrahydrofuran (6 mL) was added potassium tert-butoxide (1 mL, 1.0 M in tetrahydrofuran) at room temperature followed by stirring for 30 minutes. Then the crude 3-((2S,6R)-2,6-dimethylmorpholine-4-carbonyl)benzene-1-sulfonyl chloride (0.7 mmol; Example 147A) in tetrahydrofuran (8 mL) was added slowly. The mixture was stirred at room temperature for 3 hours. Then the mixture was concentrated. The residue was purified by chromatography on silica gel (hexane/ethyl acetate=1:1) to give crude material. The crude material was dissolved in ether (60 mL), the insoluble solid was removed, and the ether solution was concentrated to give the titled compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.90 (m, 3H), 1.10 (m, 3H), 2.83 (m, 3H), 3.30-3.60 (m, 4H), 3.80 (m, 2H), 4.37 (m, 1H), 7.00 (m, 4H), 7.20 (m, 6H), 7.71 (t, 1H, J=7 Hz), 7.88 (m, 1H), 8.00 (m, 2H); MS (ESI) m/z 519 (M+H)+.

Provenance & Evidence