Lithium Hydroxide → benzyl (3R,4R)-3-fluoro-4-hydroxypiperidine-1-carboxylate

Participants

Reaction Steps

To a solution of benzyl trans-3-fluoro-4-[(4-nitrobenzyl)oxy]piperidine-1-carboxylate (180 g, 0.45 mol) in THF/H2O (1500 mL) was added LiOH (39 g, 0.9 mol) in portions at 0° C. After the addition, the reaction mixture was allowed to warm to room temperature and stirred overnight. TLC (EtOAc:petroleum ether=1:2) showed the starting material was consumed completely. The reaction mixture was extracted with EtOAc (3×500 mL). The combined organic layers were washed with brine (800 mL), dried over anhydrous Na2SO4 and concentrated to a crude residue. The residue was purified by column chromatography (EtOAc:petroleum ether=1:20) to afford benzyl trans-3-fluoro-4-hydroxypiperidine-1-carboxylate as a white solid.

Provenance & Evidence