Sodium borohydride → HCID 86635467, compound

Participants

Reaction Steps

(+/−)-3-{4-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-butyric acid ethyl ester (0.581 g, 1.19 mmol) is dissolved in THF (15 mL) and methyl alcohol (3 mL). Sodium borohydride is added portionwise until an excess has been added. After stirring at room temperature for 3 days, the reaction is quenched with water followed by 1N HCl. The resulting mixture is extracted two times with ethyl acetate. The organic layers are combined, washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is purified via flash chromatography eluting with 5-10% ethyl acetate:toluene to give the title compound. 1H NMR (CDCl3) δ 1.134 (d, 3H), 1.262 (d, 6H), 1.456 (s, 2H), 1.764 (m, 2H), 2.223 (s, 3H), 2.939-3.039 (m, 2H), 3.476-3.539 (m, 2H), 4.747 (s, 2H), 6.516 (d, 1H), 6.559 (dd, 1H), 6.99 (d, 1H), 7.263 (t, 1H), 7.372 (d, 2H), 7.663 (s, 1H)

Provenance & Evidence