Sodium hydride → 4-Benzhydryl-1-[2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)ethyl]piperazin-2-one

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Reaction Steps

To a solution of product from Example 64C (0.11 g, 0.4 mmol)) in N,N-dimethylformamide was added a 60% dispersion of sodium hydride in mineral oil (0.03 g, 0.75 mmol) and the reaction mixture was stirred at room temperature for 1 hour. Then 1-(2-bromoethyl)-3,3-diphenylpyrrolidin-2-one (Example 64B, 0.142 g, 0.4 mmol) was added, and the reaction mixture was stirred at ambient temperature overnight. The reaction mixture was concentrated and partitioned in water/methylene chloride. The organic layer was separated, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed, eluting first with 5% ethyl acetate/hexane and then eluting the title compound with 15% methanol/methylene chloride. 1H NMR (300 MHz, CDCl3) δ ppm 7.31 (m, 20H), 3.48 (t, J=6.44 Hz, 2H), 3.42 (m, 2H), 3.28 (m, 2H), 3.12 (s, 2H), 2.70 (m, 2H), 2.66 (m, 2H), 2.42 (m, 2H); MS (ESI+) m/z 530 (M+H)+.

Provenance & Evidence