Sodium borohydride → HCID 70654850, compound

Participants

Reaction Steps

A solution of the crude N-[rel-(S)-1-((3S,4R)-4-cyanomethylsulfanyl-tetrahydro-furan-3-yl)-1-(2-fluoro-phenyl)-ethyl]-2,2,2-trifluoro-acetamide (2 g, 3.19 mmol) in ethanol (60 ml) was reacted with sodium borohydride (482 mg, 12.8 mmol) at 0° C. The reaction was left to warm to room temperature and stirred overnight. For the workup, the reaction mixture was extracted with a mixture of a saturated solution of sodium hydrogencarbonate and ethyl acetate. The combined organic layers were dried over sodium sulphate and evaporated at reduced pressure. The residue was purified by flash chromatography on silica gel using a gradient of heptane and ethyl acetate=100:0 to 0:100 as the eluent. The {rel-(3R,4S)-4-[(S)-1-amino-1-(2-fluoro-phenyl)-ethyl]-tetrahydro-furan-3-ylsulfanyl}-acetonitrile (510 mg, 57% yield) was obtained as a light yellow oil. MS (ISP): m/z=281.0 [M+H]+.

Provenance & Evidence