[CH3:1][O:2][C:3]([C:5]12[CH2:12][CH2:11][C:8]([C:13]3NC4C(=O)N(CCC)C(=O)N(CCC)C=4N=3)([CH2:9][CH2:10]1)[CH2:7][CH2:6]2)=[O:4].C(=O)([O-])[O-].[K+].[K+].C(Br)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[OH2:44]>CN(C=O)C.C(OCC)(=O)C.CCCCCC>[CH2:1]([O:2][C:3]([C:5]12[CH2:6][CH2:7][C:8]([CH2:13][OH:44])([CH2:9][CH2:10]1)[CH2:11][CH2:12]2)=[O:4])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=14-Hydroxymethylbicyclo[2.2.2]octane-1-carboxylic acid (XVII, Example 14, 24.8 g 135 mmol) is dissolved in DMF (950 ml). Anhydrous potassium carbonate (25 g, 181 mmol) is added to the solution slowly. Benzyl bromide (22 g, 12.94 mmol) is then added. The reaction mixture is heated at 80° for 16 hr. To the reaction mixture is added water (150 ml) and concentrated to give an oil, which was dissolved in ethyl acetate/hexane (5/1, 500 ml). The mixture is washed with saline (2×200 ml), dried over anhydrous sodium sulfate and concentrated to give the title compound, NMR (400 MHz, CDCl3) δ 7.39, 5.11, 3.28, 1.84 and 1.41.
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