Hydrochloric Acid → 6-(2-Phenylethyl)quinuclidin-3-one

Participants

Reaction Steps

A suspension of tBuOK in toluene was heated under reflux, and a solution of methyl 1-(2-ethoxy-2-oxoethyl)-2-(2-phenylethyl)piperidine-4-carboxylate in toluene was added dropwise thereto, followed by stirring at the same temperature for 15 hours. After cooling to room temperature, concentrated hydrochloric acid was added thereto. The aqueous layer was separated and the organic layer was extracted with concentrated hydrochloric acid. The hydrochloric acid layer was heated under reflux for 15 hours. The reaction mixture was neutralized by addition of K2CO3 and the aqueous layer was extracted with CHCl3. The organic layer was dried and then concentrated under reduced pressure. The residue obtained was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, CHCl3:MeOH) to obtain 6-(2-phenylethyl)quinuclidin-3-one as a pale brown oil.

Provenance & Evidence