Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-methoxycarbonylvinyl)indol-1-ylmethyl]-3-methoxybenzoate

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Reaction Steps

A solution of t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-formylindol-1-ylmethyl]-3-methoxybenzoate (1.2 g) and methyl (triphenylphosphoranylidene)acetate (1.8 g) in dioxane (12 ml) was heated at reflux for 48 hours. The solvent was evaporated. The resultant residue was purified by flash chromatography on silica gel (600 ml), eluting with 3:7 ethyl acetate:hexane, to give t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-methoxycarbonylvinyl)indol-1-ylmethyl]-3-methoxybenzoate (1.1 g, 84%) as a yellow solid; mp 163°-164°.

Provenance & Evidence