Dimethylformamide → 2-[3-(2-Naphthyl)-8-azabicyclo[3.2.1]oct-2-en-8-yl]ethanol

Participants

Reaction Steps

3-Naphthalen-2-yl-8-aza-bicyclo[3.2.1]oct-2-ene (1.00 g, 4.25 mmol), 1.05 g (8.40 mmol) 2-bromoethanol, 1.70 g (12.6 mmol) K2CO3 and 57 mL of DMF are stirred at 80 C for 12 h. The reaction mixture is poured into 300 mL of cold H2O and extracted with 3×50 mL of EtOAc. The combined organics are washed with 3×100 mL of H2O, 1×100 mL of brine, dried over MgSO4, filtered, and the volatiles are evaporated to give 1.08 g (3.87 mmol, a 91% yield) of the title compound as a white solid. mp: 113-114° C.; MS (ES) m/z 280 (MH)+.

Provenance & Evidence