反应详情

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)+.

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)