(+)-Ursolic Acid → HCID 49773832, compound

Participants

Reaction Steps

To a mixture of ursolic acid (2a, 1.0 g, 2.18 mmol) and CH2Cl2 (55 mL) was added the Dess-Martin reagent (1.2 g, 2.83 mmol) under nitrogen at room temperature. After stirring at room temperature for 2.5 hours, the starting material was consumed as indicated by TLC (1:1 hexanes:diethyl ether). The reaction mixture was quenched with the addition of a solution of sodium thiosulfate and NaHCO3 (6.3 g sodium thiosulfate in 25 mL saturated NaHCO3 solution). The mixture was stirred at room temperature for 10 minutes. The layers were separated and the aqueous layer was extracted with EtOAc (3×250 mL). The combined organics were dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography (silica, 3:1 hexanes/diethyl ether) to provide the sub-title compound (924 mg, 92%) as a white foam solid.

Provenance & Evidence