Trifluoroacetic acid → 3-(Naphth-2-yl)-8-azabicyclo[3.2.1]oct-2-ene

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Reaction Steps

3-Hydroxy-3-naphthalen-2-yl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (6.80 g, 19.3 mmol) and 10 mL TFA are stirred at 23° C. in 80 mL of CH2Cl2 for 2.5 h. The volatiles are removed and the residue partitioned between 100 mL of saturated NaHCO3 and 100 mL EtOAc. The aqueous layer is extracted with 2×50 mL EtOAc, and the combined organics are washed with 3×50 mL H2O, 1×50 mL brine, dried over MgSO4, filtered, and stripped to give 4.50 g (19.1 mmol, a 100% yield) of the title compound as a white solid. MS (ES) m/z (relative intensity): 236 (M++H, 100).

Provenance & Evidence