Sodium Hydroxide → Ammonia

Participants

Reaction Steps

A mixture of 3-tert-butoxycarbonyl-3,9-diazabicyclo-[4.2.1]-nonane (1.1 g, 4.9 mmol), 3-chloro-5-ethoxypyridine (0.77 g, 4.9 mmol), potassium-tert-butoxide (1.09 g, 9.7 mmol) and 1,2-dimethoxyethane (20 ml) was heated at reflux for 1.5 h. Sodium hydroxide (30 ml, 1 M) was added and the aqueous phase was extracted twice with ethyl acetate (30 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound as an oil. Yield 0.24 g, 14%.

Provenance & Evidence