Nitric Acid → HCID 121317102, compound

Participants

Reaction Conditions

Reaction Steps

(S)-6-(difluoromethyl)-5,5-difluoro-6-(2-fluorophenyl)piperidin-2-one (880 mg, 3.15 mmol) was suspended in trifluoroacetic acid (2.55 mL). The mixture was cooled to 0° C. and concentrated H2SO4 (2.46 g, 24.3 mmol) was added. Then, HNO3 (661.61 mg, 6.30 mmol) was added dropwise. After 2 hours of stirring at 25° C., the reaction mixture was poured onto 100 g ice and basified to pH>11 using 5 M NaOH (aq). The suspension was extracted with ethyl acetate (150 mL). The phases were separated and the aqueous layer was extracted with ethyl acetate (2×70 mL). The combined organic phases were washed with a solution of saturated aqueous NH4Cl (30 mL) and water (30 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to afford (S)-6-(difluoromethyl)-5,5-difluoro-6-(2-fluoro-5-nitrophenyl)piperidin-2-one (1.00 g, crude).

Provenance & Evidence