Triacetoxyperiodinane → HCID 90204216, compound

Participants

Reaction Steps

To a solution of 5-cyclopropyl-N-[1-hydroxy-2-(5-methyl-1,2,4-oxadiazol-3-yl)propan-2-yl]-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxamide (example 113, 0.1 g, 250 μmol) in dry dichloromethane (2 ml) was added Dess-Martin periodinane (111 mg, 262 μmol). The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with dichloromethane and quenched with a 1.0M aqueous solution of sodium bicarbonate with 5% sodium thiosulfate. The bi-phasic mixture was stirred for 20 minutes and then transferred into a separatory funnel. The organic phase was dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/(solution of 3% Et3N in ethyl acetate) gradient to yield the title compound (71 mg, 71%). MS (ESI, m/z): 399.5 (M+H+).

Provenance & Evidence