Triacetoxyperiodinane → tert-Butyl 4-[4-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]piperidine-1-carboxylate

Participants

Reaction Steps

Dess-Martin periodinane (53 mg, 0.126 mmol) was added to a solution of tert-butyl 4-[({[2-{[tert-butyl(diphenyl)silyl]oxy}-1-(hydroxymethyl)ethyl]amino}carbonyl)amino]piperidine-1-carboxylate (50 mg, 0.090 mmol) in dichloromethane (20 mL) at 0° C. After 4 h, the reaction was quenched with a 1:1 mixture of saturated sodium thiosulfate and sodium bicarbonate solution. The mixture was extracted with dichloromethane (2×) and the combined organic extracts were dried over sodium sulfate, filtered, concentrated. Purification by silica gel chromatography (100% dichloromethane→9% methanol {1% ammonium hydroxide)/dichloromethane} gave the title compound (25 mg). MS 536.3 (M+1)

Provenance & Evidence