p-Toluenesulfonic acid → HCID 69058271, compound

Participants

Reaction Steps

A solution of the product of (3aS,4R,6aS,7R,10S,10aS)-7-(2,2-difluoro-1-methylvinyl)-2,2,5,10-tetramethyl-4,6a,7,8,9,10-hexahydro-3aH-naphtho[1,8a-d][1,3]dioxol-4-yl acetate (Preparation 151, 400 mg) and para-toluenesulfonic acid in methanol (20 ml) was stirred at room temperature for 24 hours. The reaction mixture was quenched with excess aqueous sodium hydrogen carbonate, diluted with water and extracted with diethyl ether (2×). The combined organic phases were washed with concentrated aqueous sodium chloride, dried (Na2SO4) and evaporated. The solid residue was purified by flash column chromatography on silica gel eluting with ethyl acetate:hexane (5:95 and then 10:90) to give the product as a white solid (195 mg).

Provenance & Evidence