Dichloromethane → HCID 131732642, compound

Participants

Reaction Conditions

Reaction Steps

A two-necked flask (internal volume: 30 mL) charged with magnetic stir bars was charged with demethylated quinine (quinine-OH) (465.6 mg, 1.5 mmol). The flask was cooled to 0° C., triethylamine (238 μL, 1.1 equiv.), dichloromethane (3.0 mL), and trifluoromethanesulfonyl chloride (166 μL, 1.05 equiv.) were added to the flask, and the mixture was reacted at room temperature with stirring. After 8 hours, the reaction was quenched by adding a saturated sodium hydrogen carbonate aqueous solution (5 mL) to the reaction mixture, and the reaction mixture was separated into two layers. The organic layer (dichloromethane solution) was isolated preparatively, and 15 mL of dichloromethane was added to the aqueous layer to extract the product. The above operation was repeated four times. An excess amount of anhydrous magnesium sulfate was added to the collected organic layer (dichloromethane solution), and the mixture was filtered. The solvent was evaporated under reduced pressure to obtain a concentrate including a crude product. The concentrate was sequentially subjected to silica gel flash column chromatography (eluant: chloroform/methanol=9/1, Rf=0.26)) and reversed-phase high-performance liquid chromatography (eluant: water and acetonitrile (gradient)) to obtain quinine triflate (white solid, 265.9 mg) (see below). The yield thereof was 40%.

Provenance & Evidence