Hydrochloric Acid → 4-Hydroxy-4-(6-benzyloxynaphth-2-yl)piperidine

Participants

Reaction Steps

A solution of 4.5 gm (10.4 mMol) 1-tert-butoxycarbonyl-4-hydroxy-4-(6-benzyloxynaphth-2-yl)piperidine, 5 mL 5N hydrochloric acid in 20 mL ethyl acetate and 20 mL tetrahydrofuran was stirred at room temperature for 18 hours. The reaction mixture was then partitioned between ethyl acetate and 2N sodium hydroxide. The phases were separated and the aqueous phase extracted well with ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, eluting with 10% methanol in dichloromethane. Fractions containing product were combined and concentrated under reduced pressure to provide 0.814 gm (24%) of the title compound.

Provenance & Evidence