Tetrahydrofuran → Enrasentan

Participants

Reaction Steps

A 10 mL three-necked flask equipped with reflux condenser was charged with [1S -(1α, 2α, 3α)]-methyl 1-(1,3-benzodioxol-5-yl)-2,3-dihydro-3-[2-(2-hydroxyethoxy)-4-methoxyphenyl]-5-propoxy-1H-indene-2-carboxylate (34 mg, 0.071 mmol), THF (1 mL), MeOH (0.5 mL) and LiOH—H2O (15 mg, 0.355 mmol). The solution was heated to reflux for 12 h, cooled to room temperature and acidified with citric acid monohydrate (40 mg, 0.19 mmol) to pH 3.0. Upon complete hydrolysis, EtOAc (20 mL) and H2O (20 mL) was added, the organic phase washed with brine (15 mL), dried (MgSO4) and concentrated in vacuo affording (+) (1S, 2R, 3S)-3-[2-(2-hydroxyeth-1-yloxy)-4methoxyphenyl]-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid as a white solid (30 mg, 81%).

Provenance & Evidence