Triacetoxyperiodinane → HCID 11341642, compound

Participants

Reaction Steps

Solid (±)-3-(1-(3-(5-(hydroxymethyl)pyridin-2-yl)-4-(7-methyl-1H-indazol-5-yl)butanoyl)piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-one (20.9 mg, 0.025 mmol, 1.0 equiv) and Dess-Martin reagent (21.8 mg, 2.0 equiv) were dissolved in anhydrous methylene chloride (2 mL). The cloudy solution was stirred at room temperature for 1 h. The reaction was quenched with 0.5 N sodium hydroxide. The layers were separated and the organic layer was washed with brine, dried over sodium sulfate and concentrated to give an off-white solid. Purification by flash column chromatography (10% MeOH in methylene chloride) afforded the desired product (9.5 mg, 69%) as a colorless oily solid. 1H-NMR (400 MHz, CDCl3) δ 10.02 (d, J=8.0 Hz, 1H), 9.06 (d, J=16.4 Hz, 1H), 7.94-7.82 (m, 2H), 7.18-7.08 (m, 4H), 7.08-6.84 (m, 3H), 6.65 (d, J=7.6 Hz, 1H), 4.68-4.44 (m, 2H), 4.24, 4.16 (2s, 1H), 4.05-3.95 (m, 1H), 3.88-3.76 (br. 1H), 3.30-2.92 (m, 4H), 2.72-2.47 (m, 2H), 2.47 (s, 3H), 1.84-1.35 (m, 6H).

Provenance & Evidence