Triacetoxyperiodinane → HCID 66731706, compound

Participants

Reaction Steps

To a stirred solution of tert-butyl-4-hydroxy-2-isobutylpiperidine-1-carboxylate (4.6 g, 0.018 mol) in DCM (50 mL) at 0° C., 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (9.1 g, 0.02146 mol) was added portionwise and the resulting solution was warmed to room temperature and stirred under N2 overnight. The reaction mixture was quenched with satd NaHCO3 solution (50 mL) and was filtered through a Celite® pad. The filtrate was extracted several times with DCM (50 mL), the combined organic phases were washed with water (50 mL), brine (50 mL), dried over Na2SO4 and concentrated. The concentrated product was purified by column chromatography using 10% EtOAc in petroleum ether to yield the product with HPLC purity 90%. The impure product was further purified by preparative HPLC to yield 2-isobutyl-4-oxo-piperidine-1-carboxylic acid tert-butyl ester as a liquid (2.1 g, 46%).

Provenance & Evidence