Sodium borohydride → HCID 68089094, compound

Participants

Reaction Steps

(4-Fluorophenyl)(3-vinyl-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone (50 mg, 0.2 mmol; prepared as described above) was dissolved in CH2Cl2:MeOH (9:1, 15 mL) and cooled in a dry ice/acetone bath. Ozone was bubbled through the solution for 3 min and the reaction was allowed to warm to RT as then purged with an air inlet for 5 min. Sodium borohydride (65 mg, 1.7 mmol) in MeOH (10 mL) was added and the reaction allowed to stir for 1 h. The reaction mixture was concentrated, partitioned between water and EtOAc, and the water layer extracted with CH2Cl2:butanol (9:1). The volatiles were removed under reduced pressure to give 40 mg of crude product. The crude (4-fluorophenyl)(3-(hydroxymethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone was used in the next step without further purification. LC-MS (M+H)=287.2.

Provenance & Evidence