Sulfuric Acid → HCID 58695824, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 3-[4-chloro-2-(1-hydroxypropyl)phenyl]-8-azabicyclo[3.2.1]octane-8-carboxylate (2-8) (2.25 g, 6.39 mmol) in acetonitrile (100 mL) was add concentrated H2SO4 (5.11 mL, 95.9 mmol) in 50 mL of acetonitrile. The mixture was stirred at 60° C. for 1 h, quenched with 1 N NaOH (200 mL), and extracted with EtOAc (3×200 mL). The combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. Purification of the crude residue by flash chromatography over silica gel (a mixture of 9:1:0.1 methylenechloride:MeOH:30% NH4OH as eluent) afforded (2-9) as a white solid.

Provenance & Evidence