HCID 53673921, compound → HCID 15383498, compound

Participants

Reaction Steps

(+/-)-3-(3-pyridyl)-2-carboethoxy-2-azabicyclo[2.2.2]octane (XII) (500 mg, 1.92 mmol) was dissolved in a solution of 20% (w/v) NaOH in absolute ethanol (10 mL) and refluxed for 24 h. The organic solvent was evaporated on a rotary evaporator. The pH of the basic residue was adjusted to 9 by addition of a solution of 2N HCl in water and was extracted with ethyl acetate (4×10 mL). The organic extracts were dried over anhydrous K2CO3, and concentrated. The resulting oily residue was purified by distillation under reduced pressure (108°-110° C./0.4 mm Hg) to afford 300 mg (83%) of compound (XIII). 1H NMR (CDCl3): δ 8.62-8.61 (d, 1H), 8.44-8.41 (m, 1H), 7.80-7.72 (m, 1H), 7.24-7.21 (m, 1H), 4.30 (s, 1H), 3.71-3.63(m, 1H), 2.20(m, 1H), 2.0-1.51 (m, 8H), 1.42 (d, 1H).

Provenance & Evidence