Trifluoroacetic acid → HCID 67551142, compound

Participants

Reaction Steps

A solution of the 2-[(3-cyano-1H-indol-5-yl)-hydroxy-methyl]-cyclopropane-carboxylic acid ethyl ester (1.0 g, 3.5 mmol), dichloromethane (25 ml), and trifluoroacetic acid (5 ml) was cooled to 0° C. and treated with triethylsilane (0.57 g, 5.0 mmol). The solution was stirred for 30 min and then diluted with an additional 50 ml dichloromethane and neutralized with 1 N sodium hydroxide. The organic layer was washed with brine (1×50 ml) and dried over anhydrous sodium sulfate. The filtrate was concentrated in vacuo to a deep amber oil. Silica gel column chromatography (hexanes, ethyl acetate 1:1) afforded 2-(3-cyano-1H-indol-5-ylmethyl)-cyclopropane-carboxylic acid ethyl ester (0.62 g, 56%) as a light yellow oil. LC-MS: 1.38 min; 269.1 (MH)+.

Provenance & Evidence