Tetrabutylammonium Fluoride → (R)-tert-butyl 3-((S)-1-(3-chlorophenyl)-1,5-dihydroxypentyl)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-tert-butyl 3-((S)-5-(tert-butyldimethylsilyloxy)-1-(3-chlorophenyl)-1-hydroxypentyl)piperidine-1-carboxylate (511 mg, 1 mmol) in CH3CN (10 mL) was added tetrabutylammonium fluoride (550 mg, 2 mmol) in one portion. The reaction mixture was stirred at 60° C. for 2 h. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel with EtOAc/hexane to give (R)-tert-butyl 3-((S)-1-(3-chlorophenyl)-1,5-dihydroxypentyl)piperidine-1-carboxylate (350 mg, 80%). 1H NMR (400 MHz, CDCl3): 1.05-1.42 (m, 6H), 1.46 (s, 9H), 1.52-1.79 (m, 4H), 1.94-2.03 (m, 2H), 2.55 (m, 2H), 3.56 (m, 2H), 3.97 (m, 1H), 4.36 (m, 1H), 7.20-7.25 (m, 3H), 7.37 (s, 1H). MS (E/Z): 398 (M+H+)

Provenance & Evidence