Selectfluor → HCID 23234366, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (+)-nopinone (Aldrich, 1.0 g, 7.2 mmol) in water (35 mL), was added sodium dodecyl sulfate (Aldrich, 2.1 g, 7.2 mmol). The mixture was heated to 80° C. and then 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane tetrafluoroborate (Alfa-aesar, 2.8 g, 8.0 mmol) was added in two portions with one hour interval and stirred at 80° C. overnight. The reaction mixture was cooled and extracted with diethyl ether (3×30 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, 0-20% of ethyl acetate in hexanes) to obtain 0.4 g of the title compound. MS (DCI/NH3) m/z 174 (M+NH4)+.

Provenance & Evidence