反应详情

A solution of methyl 3-hydroxycyclopentanecarboxylate A-11 (500.0 mg, 3.00 mmol) in anhydrous toluene (10.0 mL) was added to a solution of 5-bromopyridin-2-ol (522.0 mg, 3.00 mmol) in anhydrous toluene (10.0 mL) at room temperature. Diisopropyl azodicarboxylate (1.57 g, 6.00 mmol) was then added dropwise, and the yellow-orange solution was stirred at room temperature for 12 h. The reaction mixture was then quenched with methanol (1.0 mL) and concentrated to dryness under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexanes to ethyl acetate gradient) to give methyl 3-(5-bromopyridin-2-yloxy)cyclopentane carboxylate A-12 (462.0 mg, Yield=51%). MS (ESI), [M+Na]+ 321, 323.

1. customThe reaction mixture was then quenched with methanol (1.0 mL)
2. concentrationconcentrated to dryness under reduced pressure
3. customThe residue was purified by flash column chromatography on silica gel (hexanes to ethyl acetate gradient)