Triphenylphosphine → 4-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-7-ethoxy-6-methyl-3,4-dihydro-1,4-benzoxazepin-5(2H)-one

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Reaction Steps

A solution of triphenylphosphine (0.176 g, 0.671 mmol) in THF (5 mL) in an ice bath was treated with diisopropyl azodicarboxylate (0.140 mL, 0.67 mmol) dropwise. After 10 minutes, N-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-3-ethoxy-6-hydroxy-N-(2-hydroxyethyl)-2-methylbenzamide (114e, 0.155 g, 0.334 mmol) was added in one portion. The reaction mixture was stirred in the ice bath overnight and the reaction mixture gradually warmed to room temperature. The reaction mixture was concentrated under vacuum and purified by column chromatography (0-40% ethyl acetate/heptane) to give 4-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-7-ethoxy-6-methyl-3,4-dihydro-1,4-benzoxazepin-5(2H)-one (114f, 0.087 g, 58%) as a clear, thick oil.

Provenance & Evidence