Triacetoxyperiodinane → HCID 59178537, compound

Participants

Reaction Steps

To a solution of 282 mg of methyl rel-5-fluoro-6-[(3R,4R)-4-(hydroxymethyl)-3-phenylpiperidin-1-yl]nicotinate in 3.0 mL of dichloromethane was added 382 mg of Dess-Martin Periodinane at room temperature, followed by stirring for 1.5 hours. This reaction mixture was washed with 1,2-dichloroethane, transferred to a dropping funnel, and added dropwise to a mixture of 147 mg of (1R)-1-(1-naphthyl)ethaneamine, 521 mg of sodium triacetoxyborohydride, 49 mg of acetic acid, and 10 mL of 1,2-dichloroethane at room temperature. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, followed by vigorously stirring for 10 minutes, and then extraction with chloroform. The organic layer was washed with water and saturated brine in this order, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by NH silica gel (FUJI SILISIA CHEMICAL. Ltd., Japan) column chromatography (hexane-ethyl acetate) to obtain 314 mg of methyl 5-fluoro-6-[4-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]nicotinate as a colorless foamy substance.

Provenance & Evidence