Water → HCID 86227318, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-(4-{2-[5-(1H-imidazol-1-ylcarbonyl)thiophen-2-yl]ethyl}-1,3-thiazol-2-yl)acetamide (220.0 mg, 0.635 mmol) in anhydrous tetrahydrofuran (17.6 ml) was cooled to 0° C., and water (4.4 ml) and sodium borohydride (240.2 mg, 6.350 mmol) were added. After stirring at 0° C. for 1.5 hr, the reaction mixture was concentrated to about 2 ml, and saturated aqueous ammonium chloride (20 ml) was added dropwise. This was extracted 3 times with ethyl acetate, and the combined organic layer was washed with aqueous ammonium chloride and saturated brine. The mixture was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 100 g, ethyl acetate:hexane=2:1) to give N-(4-{2-[5-(hydroxymethyl)thiophen-2-yl]ethyl}-1,3-thiazol-2-yl)acetamide (157.1 mg, 0.556 mmol, yield 87.6%) as a white solid.

Provenance & Evidence