Ammonium Chloride → ethyl 2-[5-(methylsulfanyl)pyridin-2-yl]-3-(tetrahydro-2H-pyran-4-yl)propanoate

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Reaction Steps

To a solution of ethyl 2-[5-(methylsulfanyl)pyridin-2-yl]-3-(tetrahydro-2H-pyran-4-yl)-2-propenoate (2.41 g) in methanol (20 mL) was added sodium borohydride (890 mg), and the mixture was stirred at room temperature for 3 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium to sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the title compound (1.44 g, yield 59%) was obtained as a yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio).

Provenance & Evidence