Lithium borohydride → (S)-1-(1-(3-chloro-5-(hydroxymethyl)pyridin-2-yl)piperidin-4-yl)-3-(2-fluoro-4-(methylsulfonyl)phenylamino)pyrrolidin-2-one

Participants

Reaction Steps

To a solution of (S)-methyl 5-chloro-6-(4-(3-(2-fluoro-4-(methylsulfonyl)phenylamino)-2-oxopyrrolidin-1-yl)piperidin-1-yl)nicotinate (0.20 g, 0.38 mmol) in THF (20 mL) was added LiBH4 (2 M in THF, 0.19 mL, 0.38 mmol) and the reaction was stirred overnight at ambient temperature. The reaction was diluted with DCM (50 mL) and the organic layer was washed with water (20 mL), 1 N HCl (10 mL), 1 N NaOH (10 mL) and brine (10 mL), and the combined organic phases were dried over MgSO4, filtered and concentrated under vacuum. The crude material was purified on silica using EtOAc as eluent to yield a solid, which was further triturated with isopropanol/hexanes to give (S)-1-(1-(3-chloro-5-(hydroxymethyl)pyridin-2-yl)piperidin-4-yl)-3-(2-fluoro-4-(methylsulfonyl)phenylamino)pyrrolidin-2-one (0.021 g, 0.043 mmol, 11% yield). Mass spectrum (apci) m/z=497.0 (M+H+).

Provenance & Evidence