Sulfuric Acid → HCID 67545269, compound

Participants

Reaction Conditions

Reaction Steps

4-Tolylhydrazine hydrochloride (1.90 g, 12.0 mmol) and tert-butyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate (2.70 g, 12.0 mmol; Fluka) were heated at 50° C. in anhydrous dioxane (80 mL) for one hour. Sulfuric acid (3.2 mL) was added dropwise, and the resulting mixture was heated at 80° C. overnight. After cooling the mixture to room temperature, the dioxane phase was decanted. The remaining residue was dissolved in methanol (12 mL) and added slowly to a stirred solution of concentrated ammonium hydroxide (30 mL) kept at room temperature with a water bath. The resulting mixture was extracted with ethyl acetate (3×), and the combined organic phases were washed with brine, dried (sodium sulfate), concentrated, and purified by chromatography (silica gel, 0-5% gradient of concentrated aqueous ammonium hydroxide in acetonitrile) to afford the title compound: 1H NMR (300 MHz, methanol-d4) δ ppm 1.59-1.72 (m, 1H), 1.93-2.25 (m, 3H), 2.54 (d, J=16, 1H), 3.25 (dd, J=16, 4.7, 1H), 3.91-3.99 (m, 1H), 4.49 (d, J=4.8, 1H), 6.83 (d, J=8.2, 1H), 7.12 (d, J=8.2, 1H), 7.19 (s, 1H); MS (ESI) m/z 213 (M+H)+.

Provenance & Evidence