3,3-Diphenyl-2-pyrrolidinone → 3,3-Diphenylpyrrolidine

Participants

Reaction Steps

In a 500 mL flask containing 3,3-diphenylpyrrolidine-2-one (5.00 g, 21 mmol; Example 1A) as a suspension in ether (300 mL) was added lithium aluminum hydride (2.0 M in tetrahydrofuran, 24 mL, 48 mmol) slowly via syringe under nitrogen. The reaction was refluxed overnight, cooled to room temperature, and then carefully quenched by the slow addition of 1 N NaOH (60 mL). The reaction was diluted with ethyl acetate (200 mL) and filtered through a pad of diatomaceous earth. The organic phase was separated, concentrated, and the residue purified over silica gel eluting with 95:5 dichloromethane/methanol to give the title compound. MS (DCI+) m/z 224 (M+H)+.

Provenance & Evidence