3-(3-Pyridyl)-2-carboethoxy-2-azabicyclo[2.2.2]oct-5-ene → HCID 53673921, compound

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Reaction Steps

A solution of the (+/-)-endo and (+/-)-exo isomers of 3-(3-pyridyl)-2-carboethoxy-2-azabicyclo[2.2.2]oct-5-ene, compound (II), (750 mg, 2.90 mmol) in glacial acetic acid (0.5 mL) and Pd/C (10%) was shaken under a H2 atmosphere in a Parr apparatus for 2 hours. The catalyst was removed by Alteration over a bed of Celite and the filterate was basified by addition of a solution of 40% of NaOH in water. The aqueous basic solution was extracted with dichloromethane (4×20 mL) to give 740 mg (98%) of compound (XII). 1H NMR (CDCl3 ): δ 8.48 (m, 2H), 7.60 (m. 2H), 4.78 and 4.67 (m,1H), 4.30 (m, 1H), 4.13 and 4.10 (q, 2H), 2.19 (m, 2H), 1.90 (m, 3H), 1.63 (m, 4H,), 1.28 and 0.90 (t, 3H).

Provenance & Evidence