Nitric Acid → HCID 16061668, compound

Participants

Reaction Steps

A solution of 10 (8═H, R2═COCF3; 76 mg, 0.2 mmol) in DCM (1.5 mL) was cooled to 0° C. and fuming nitric acid (21 μl, 0.5 mmol) was added in portions. The ice/water bath was removed and the reaction mixture turned red. After 10 min the reaction was quenched with aqueous NaHCO3, extracted with DCM, dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by column chromatography on silica (Heptane:Ethyl acetate=7:3) followed by preparative HPLC. Freeze-drying from acetonitrile/H2O afforded rel-2,2,2-trifluoro-N-[(2R,10R,14bR)-1,2,3,4,10,14b-hexahydro-10-methyl-8-nitrodibenzo[c,f]pyrido[1,2-a]azepin-2-yl]acetamide) (10, R8═NO2, R2═COCF3; 6 mg, 7%. Data: (m/z)=420 (M+H)+.

Provenance & Evidence