2,6-Lutidine → HCID 86675089, compound

Participants

Reaction Conditions

Reaction Steps

Osmium tetroxide (5% in water, 2.0 mL, 0.33 mmol, 0.025 equiv) was added to a biphasic mixture of benzyl 2-allyl-4-oxo-3,4-dihydroquinoline-1(2H)-carboxylate (1A) (4.20 g, 13.1 mmol, 1 equiv), sodium periodate (11.2 g, 52.3 mmol, 4.00 equiv) and 2,6-lutidine (3.04 mL, 26.1 mmol, 2.0 equiv) in water (33 mL) and dioxane (98 mL) at 23° C. The reaction mixture was stirred at 23° C. for 3 h, and then it was partitioned between water and dichloromethane. The aqueous layer was further extracted with dichloromethane (1×), and the combined organic layers were dried over sodium sulfate. The dried solution was filtered, and the filtrate was concentrated. The residue was purified by flash-column chromatography (15% ethyl acetate-hexanes, grading to 70% ethyl acetate-hexanes) to afford 25A. [M+H]+: 324.1

Provenance & Evidence