Triphenylphosphine → 1-Tert-butoxycarbonyl-4-(3-chlorophenyl)-2(s)-[2-(2-cyano-5-methoxycarbonylphenoxy)ethyl]-5-oxo-piperazine

Participants

Reaction Steps

To a solution of 250 mg of methyl 4-cyano-3-hydroxybenzoate (1.42 mmol), as described in Example 4, Step C, and PPh3 (465 mg, 1.77 mmol) in THF (10 mL) was added dropwise a solution of the alcohol from Step E above (503 mg, 1.42 mmol) and DEAD (0.28 mL, 1.77 mmol) in THF (5 mL). After stirring for 16 hr, the solution was concentrated in vacuo and the residue taken up in EtOAc. This was then washed with 10% citric acid solution, saturated NaHCO3 solution, brine and dried over MgSO4. Filtration and removal of the solvent afforded an oil. Column chromatography (silica gel; hexane:EtOAc 4:1) afforded the title compound as a clear oil.

Provenance & Evidence