Triethylamine → HCID 86731569, compound

Participants

Reaction Steps

A solution of 5-fluoro-2-{[(3S,6R)-1-(4-methoxybenzyl)-6-methylpiperidin-3-yl]ethynyl}pyridine (276 mg, 0.82 mmol) and triethylamine (0.23 mL, 1.6 mmol) in CH2Cl2 (5 mL) was cooled at 0° C. and treated with 1-chloroethyl chloroformate (0.18 mL, 1.6 mmol) and allowed to warm to ambient temperature. After stirring overnight, additional triethylamine (0.20 mL) and chloroethyl chloroformate (0.15 mL) was added and the reaction stirred overnight again. The reaction was quenched by addition of 1N NaOH. The layers were separated and the aqueous phase was extracted with CH2Cl2. The organics were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude residue was taken up in MeOH and heated at reflux for 2 h. The reaction was concentrated in vacuo. The crude material was purified by silica gel flash chromatography eluting with 0-10% MeOH in CH2Cl2 to provide 5-fluoro-2-{[(3S,6R)-6-methylpiperidin-3-yl]ethynyl}pyridine as an orange solid which gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 219.3 for M+H+.

Provenance & Evidence