Tert-butyl 3,7-diazabicyclo(3.3.1)nonane-3-carboxylate → tert-Butyl 7-[4-(4-cyanophenoxy)-2-butenyl]-3,7-diazabicyclo[3.3.1]-nonane-3-carboxylate

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Reaction Steps

tert-Butyl 3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (1.13 g; 5 mmol; see Example F above) was added to a stirred solution of 4-(4-cyanophenoxy)-1-chloro-2-butene (1.04 g; 5 mmol; from step (a) above) in MeCN (25 mL) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated and partitioned between diethyl ether and KHS04 (0.3 M). The aqueous layer was treated with NaOH (2M) and subsequently extracted with CH2Cl2. The organic layer was washed with water, dried, concentrated and purified using column chromatography (CH2Cl2:MeOH; 95:5) to give the title compound (0.84 g; 2.1 mmol).

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