2'-Hydroxyacetophenone → HCID 58551494, compound

Participants

Reaction Conditions

Reaction Steps

1-(2-Hydroxyphenyl)ethanone (260 μL, 2.2 mmol) was added portion-wise at room temperature to pyrrolidine (370 μL, 4.4 mmol) followed by portion-wise addition of 1-(4-tert-butyl-3-methoxy-benzoyl)piperidin-4-one (630 mg, 2.2 mmol). Anhydrous methanol (140 μL) was added and the slurry was heated at 80° C. for 3 h. The mixture was then partitioned between ethyl acetate and 1M aqueous HCl. The layers were separated and the aqueous layer was discarded. Saturated aqueous sodium bicarbonate was added and the layers were separated. The organic layer was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (0-25% ethyl acetate/hexanes) to give 1′-(4-tert-butyl-3-methoxybenzoyl)spiro[chroman-2,4′-piperidin]-4-one (840 mg, 94%) as a light yellow solid. ESI-MS m/z talc. 407.2, found 408.2 (M+1)+; Retention time: 2.07 minutes (3 min run).

Provenance & Evidence