Sodium borohydride → 1-(3-Fluoropyridin-2-yl)-3-hydroxycyclobutane-1-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(3-fluoropyridin-2-yl)-3-oxocyclobutanecarbonitrile (231 g, 1.22 mol) in a mixture of DCM (2 L) and MeOH (200 mL) was added NaBH4 portion-wise at −78° C. The reaction mixture was stirred 1 h at −78° C. and then quenched with a mixture of methanol and water (1/1). The organic layer was washed with water (500 mL×3), dried over Na2SO4, and concentrated. The residue was purified on silica gel (50% EtOAc in Hexanes) to provide the title compound as an amber oil (185.8 g, 77.5%), LRMS (M+H+) m/z 193.2.

Provenance & Evidence