Cl.[C:2]([C:5]12[CH2:12][CH2:11][C:8]([CH2:13][NH2:14])([CH2:9][CH2:10]1)[CH2:7][CH2:6]2)([OH:4])=[O:3].O.[CH3:16][C:17]([O:20][C:21](ON=C(C1C=CC=CC=1)C#N)=[O:22])([CH3:19])[CH3:18]>C1COCC1>[C:21]([CH:6]1[CH2:7][C:8]2([CH2:13][NH2:14])[CH2:11][CH2:12][C:5]1([C:2]([OH:4])=[O:3])[CH2:10][CH2:9]2)([O:20][C:17]([CH3:19])([CH3:18])[CH3:16])=[O:22]A sample of 8.79 g (40.0 mmol) of 4-carboxybicyclo[2.2.2]octanemethylamine hydrochloride salt suspended in 100 ml each of THF and H2O was treated with 20.0 ml (14.6 g=3.3 equiv.) of TEA, followed by 11.8 g (47.9 mmol) of BOC-ON reagent. All went into solution, and after stirring 24 hr the solution was concentrated in vacuo to a volume of about 50 ml and partitioned between 100 ml of ether and 300 ml of H2O. After addition of about 2 ml of TEA the aqueous layer was washed with ether (3×), each ether in turn washed with H2O, and the combined aqueous layer was acidified with 5% KHSO4 to give the title compound as a white solid, isolated by filtration and drying in vacuo.
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