Trifluoroacetic acid → Ammonia

Participants

Reaction Steps

A mixture of 9-[5-ethoxy-(3-pyridyl)]-3-tert-butoxycarbonyl-3,9-diazabicyclo-[4.2.1]-nonane (0.23 g, 0.66 mmol), trifluoroacetic acid (0.75 g, 6.6 mmol) and dichloromethane (10 ml) was stirred for 3 days at room temperature. Sodium hydroxide (20 ml, 1M) was added and the phases were separated, followed by extraction with dichloromethane (20 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound. The corresponding salt was obtained, by addition of a diethyl ether and methanol mixture (9:1) saturated with fumaric acid. Yield 0.39 g, 21%. Mp. 191-192° C.

Provenance & Evidence