Triphenylphosphine → 1-[1-Tert-butoxycarbonyl-3-(1,3-dioxo-1,3-dihydrobenzo[f]isoindol-2-yl)propylamino]cyclohexanecarboxylic acid benzyl ester

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Reaction Steps

To a solution of benzyl 1-(1-tert-butoxycarbonyl-3-hydroxy-1-propylamino)cyclohexanecarboxylate (466 mg, 1.19 mmol) in dry tetrahydrofuran (12 mL) was added 1,3-dioxo-1,3-dihydrobenzo[f]isoindole (258 mg, 1.31 mmol), triphenylphosphine (344 mg, 1.31 mmol) and diethylazodicarboxylate (0.21 mL, 1.31 mmol). The resulting mixture was stirred at room temperature for 6 days. The solvent was evaporated under vacuum and the residue was chromatographed on silica gel eluting first methylene chloride and then with 2% ethyl acetate in methylene chloride to afford 1-[1-tert-butoxycarbonyl-3-(1,3-dioxo-1,3-dihydrobenzo[f]isoindol-2-yl)propylamino]cyclohexanecarboxylic acid benzyl ester as a white solid, 530 mg (78%).

Provenance & Evidence