Acetic Acid → HCID 67923326, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (2S,4R,6S)-(E)-4-(t-butyldimethylsilyloxy)-6-[2-{4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinolin-3-yl}ethen-1-yl]-2-methoxy-3,4,5,6-tetrahydro-2H-pyran [149 mg; prepared as described in Example 8(a)] in a mixture of glacial acetic acid, tetrahydrofuran and water (3:2:2 by volume; 5 ml) was stirred at 70° C. under argon and under a reflux condenser for 3 hours. The resulting clear solution was diluted with diethyl ether (50 ml), washed with water (20 ml) and then with saturated aqueous sodium bicarbonate solution (2×20 ml), dried over magnesium sulphate and evaporated. The resulting residue was subjected to flash chromatography on silica gel, using as eluant ethyl acetate containing from 0 to 50% hexane by volume, to give (2RS,4R,6S)-(E)-2,4-dihydroxy-6-[2-{4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinolin-3-yl}-ethen-1-yl]-3,4,5,6-tetrahydro-2H-pyran (78 mg) in the form of a white foam.

Provenance & Evidence