Dimethyl Sulfoxide → (4bS,8R,8aS,9aR,10S,13aR,13bR)-10-tert-butyl-7-cyclopropylmethyl-5,6,7,8,9,9a,10,13b-octahydro-10-methyl-8a,13a-ethano-4,8-methanobenzofuro[3,2-e][1,3]dioxino[4,5-g]isoquinolin-1-ol

Participants

Reaction Steps

To a solution of DMSO (2.1 ml, 28.7 mMol) in THF (10 ml), at ambient temperature, was added trimethylsilyl chloride (TMSCl) (2.7 ml, 20.8 mMol). After 30 minute agitation, a solution of compound 2 (1.5 g, 3.3 mMol) in THF (12.5 ml) was added and the mixture was stirred at ambient temperature. After 24 h reaction time at ambient temperature, the reaction conversion was about 85% at which point the reaction was quenched by addition of saturated aqueous NaHCO3 solution (100 ml). The resulting mixture was extracted with EtOAc (2×100 ml). The combined organic extracts were dried over MgSO4, filtered, and concentrated to give 2.7 g of crude product. After purification by column chromatography on silica gel, 0.52 g of the title compound 3 (34.4% yield) was obtained with a purity of >99%.

Provenance & Evidence