Hydrochloric Acid → 3-(4-Nitrophenyl)-8-azabicyclo[3.2.1]oct-2-ene

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Reaction Steps

Hydrogen chloride (22 mL of a solution 4N in dioxane) was added to a solution of tert-butyl 3-(4-nitrophenyl)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate (1.97 g; 5.96 mmol; 1.0 eq.) in DCM (20 mL) and the reaction mixture was stirred at RT. After 1 h, the reaction mixture was diluted with DCM and organic phase was washed with NaOH 1N and brine, dried over magnesium sulfate, filtered and concentrated to give the title compound as a yellow solid (1.05 g, 76%). 1H NMR (300 MHz, DMSO-d6) δ 8.16 (d, J=9.0 Hz, 2H), 7.65 (d, J=9.0 Hz, 2H), 6.82 (dt, J=6.0 Hz, 1.5 Hz, 1H), 3.74-3.69 (m, 2H), 2.76 (dd, J=17.5 Hz, 4.5 Hz, 1H), 2.17 (dd, J=17.5 Hz, 1.5 Hz, 1H), 1.92-1.68 (m, 3H), 1.56-1.46 (m, 1H). HPLC (max plot) 91.7%; Rt %1.84 min. UPLC/MS: (MS+) 231.2.

Provenance & Evidence