Sodium Bicarbonate → HCID 22141125, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-[3-(3-hexyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl]acetamide (Preparation 45, 1.5 g, 4.78 mmol) in acetonitrile (20 ml) at 0° C. was added nitronium tetrafluoroborate (1.0 g, 7.53 mmol) in several portions over 5 minutes. The mixture was stirred at 0° C. for 30 minutes and then saturated sodium hydrogen carbonate solution (30 ml) was added. The aqueous mixture was extracted with ethyl acetate (3×15 ml) and the combined extracts were dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by silica column chromatography eluting with ethyl acetate:hexane (50:50) to afford the title compound (534 mg, 32%) as pale yellow platelets.

Provenance & Evidence