Chloromethyl ethyl ether → 1-{[4-Ethoxymethoxy-2-(hex-5-enyl-methyl-carbamoyl)-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester

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Reaction Steps

To a stirred solution of the diene 1c (7.94 g, 0.02 mol) in DCM and DIPEA (9.7 ml, 6 eq) at 0° C. (ice-bath) was added chloromethylethyl ether (2.79 g, 3 eq). The reaction mixture was stirred at room temperature overnight, concentrated by rotary evaporation and purified by column chromatography on silica gel (EtOAc/petroleum ether 1:1→1:0) which gave the pure title compound as slightly yellow syrup (6.67 g, 74%).

Provenance & Evidence