Potassium Phosphate, Tribasic → HCID 86691702, compound

Participants

Reaction Conditions

Reaction Steps

Step-III: To a stirred solution of acetic acid (3S,4R,5S,6S)-4,5-diacetoxy-6-[4-bromo-3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-phenyl]-2-methoxy-tetrahydro-pyran-3-yl ester (700 mg, 1.18 mmol) in toluene (11 ml) was added tricyclohexylphosphine (132 mg, 0.47 mmol), a solution of potassium phosphate tribasic (1.0 g, 4.72 mmol) in water (1 ml), ethylboronic acid (262 mg, 3.54 mmol). The reaction mixture was degassed for 40 min then added palladium (II) acetate (39 mg, 0.18 mmol). Reaction mixture was stirred at 90° C. for overnight. Reaction mixture was cooled to room temperature and was filtered through celite bed, washed with ethyl acetate (10 ml). Organic layer was washed with water (15 ml) followed by brine (15 ml), dried over sodium sulfate, concentrated and purified by column chromatography to give 320 mg of acetic acid (3S,4R,5S,6S)-4,5-diacetoxy-6-[3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-4-ethyl-phenyl]-2-methoxy-tetrahydro-pyran-3-yl ester as white solid.

Provenance & Evidence