Trifluoroacetic acid → Ammonia

Participants

Reaction Steps

A mixture of 5-[6-phenylethynyl-pyridazin-3-yl]-(1S,4S)-2,5-diaza-bicyclo-[2.2.1]heptane-2-carboxylic acid tert-butyl ester (1.95 g; 5.2 mmol), trifluoroacetic acid (8.0 ml; 104 mmol) and dichloromethane (20 ml) was stirred for 2 hours at room temperature. Aqueous sodium hydroxide (20 ml; 4 M) was added. The mixture was extracted with dichloromethane (3×20 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound as free base. Yield 0.85 g (59%). The corresponding salt was obtained by addition of a diethyl ether and methanol mixture (9:1) saturated with fumaric acid. Mp. 173.1-174.4° C.

Provenance & Evidence