Tetrabutylammonium Fluoride → [5-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3,4-thiadiazol-2-yl]methanol

Participants

Reaction Steps

To a solution of 2-({[tert-butyl(diphenyl)silyl]oxy}methyl)-5-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3,4-thiadiazole (122 mg) in tetrahydrofuran (1.2 mL) was added tetrabutylammonium fluoride (0.44 mL: 1M tetrahydrofuran solution), and the mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with ethyl acetate, and washed with saturated brine. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (51.3 mg, yield 63%) was obtained as white crystals from a fraction eluted with ethyl acetate-hexane (19:1, volume ratio). melting point 208.5-208.6° C. MS: 474 (MH+).

Provenance & Evidence