Tetrahydrofuran → 1-{[6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]oxy}propan-2-ol

Participants

Reaction Steps

To a solution of 1-[([6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl]-1H-pyrrol-2-yl)pyridin-3-yl]oxy}propan-2-one (0.050 g) in a mixed solvent of tetrahydrofuran (5 mL) and ethanol (1 mL) was added sodium borohydride (18 mg) under ice-cooling. The reaction solution was warmed to room temperature, and stirred at room temperature for 10 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-100:0, volume ratio), and recrystallized from hexane-ethyl acetate to give the title compound (0.039 g, yield 78%) as colorless crystals. MS: 511 (MH+). melting point 116-118° C.

Provenance & Evidence