Pyridine → HCID 86630119, compound

Participants

Reaction Steps

To a solution of 1.0 g (2.8 mmol) of tert-butyl 4-hydroxy-4-[4-(hydroxymethyl)-2-naphthyl]piperidine-1-carboxylate in 10 mL of anhydrous dichloromethane under an atmosphere of nitrogen was added 0.34 mL (4.2 mmol) of pyridine then 1.9 g (4.5 mmol) of Dess-Martin periodinane and the resulting solution was stirred at ambient temperature for 2 h. The mixture was diluted with a saturated aqueous sodium bicarbonate solution (5 mL), the layers were separated and the aqueous phase extracted with dichloromethane (3×10 mL). The combined organic layers were washed with brine (25 mL), dried over magnesium sulfate, filtered and evaporated in vacuo to yield the crude title compound as a colorless oil.

Provenance & Evidence