Sodium borohydride → HCID 66718163, compound

Participants

Reaction Steps

To a solution of 6-[3-butyl-5-(1,2-dihydroxy-2-phenylethyl)-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (890 mg, 2.09 mmol) in benzene (10 mL) was added lead tetraacetate (1.39 g, 3.13 mmol) with benzene (5 mL) and the reaction was stirred at room temperature for 45 min. The suspension was filtered over celite and the filtrate was concentrated to a yellow oil. The oil was taken up in methanol (20 mL) and sodium borohydride (198 mg, 5.24 mmol) was added in portions over 3 min. Upon addition, the reaction became a clear light yellow solution containing a black precipitate. After stirring at room temperature for 15 min, the mixture was filtered over celite and the filter cake was washed with methanol. The filtrate was concentrated and the residue was portioned between 0.5M aqueous hydrochloric acid and ethyl acetate. The aqueous phase was extracted two times with ethyl acetate and the combined organic phases were washed with brine, dried over sodium sulfate and concentrated to a yellow oil. The crude material was purified by chromatography (silica, heptane:ethyl acetate 1:0 to 1:1) to afford the title compound (495 mg, 68%) as a colorless oil. MS: m/e=321.2 [M+H]+.

Provenance & Evidence