tert-butyl 3,9-diazabicyclo[4.2.1]nonane-3-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 9-Methyl-3-tert-butoxycarbonyl-3,9-diazabicyclo-[4.2.1]-nonane (3.4 g, 14.1 mmol), Diethylazodicarboxylate (12.3 g, 70.7 mmol) and toluene (35 ml) was stirred at reflux for 1.5 h. Sodiumhydroxide (50 ml, 1 M) was added. The aqueous phase was extracted twice with ethyl acetate (50 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound as an oil. Yield 1.13 g, 35%. at reflux for 1.5 h The aqueous phase was extracted twice with ethyl acetate (50 ml)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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%. was heated at reflux for 1.5 h the aqueous phase was extracted twice with ethyl acetate (30 ml)