3,3-Diphenyl-3,4,5,6-tetrahydropyridin-2-ol → HCID 4341835, compound

Participants

Reaction Steps

In a 500 mL flask containing 3,3-diphenylpiperidin-2-one (3.77 g, 15 mmol; Example 68C) as a suspension in ether (300 mL) was added lithium aluminum hydride (2.0 Min tetrahydrofuran, 15 mL, 30 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 or diatomaceous earth. The organic phase was separated, concentrated, and the residue was purified over silica gel eluting with 95:5 dichloromethane/methanol to give the title compound. MS (DCI+) m/z 238 (M+H)+.

Provenance & Evidence