Triacetoxyperiodinane → tert-Butyl 4-[4-(methoxycarbonyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]piperidine-1-carboxylate

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Reaction Steps

Dess-Martin periodinane (1.77 g, 4.16 mmol) was added to a solution of methyl N-({[1-(tert-butoxycarbonyl)piperidin-4-yl]amino}carbonyl)serinate (1.15 g, 3.33 mmol) in dichloromethane (30 mL) at 0° C. and then warmed to ambient temperature. 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, and concentrated. Purification by silica gel chromatography (100% dichloromethane→12% methanol {1% ammonium hydroxide}/dichloromethane) gave the title compound.

Provenance & Evidence