[CH:1]([N:4](CC)C(C)C)(C)C.[CH2:10]([C:15]12[CH2:22][CH2:21][C:18]([C:23]([OH:25])=O)([CH2:19][CH2:20]1)[CH2:17][CH2:16]2)[CH2:11][CH2:12][CH2:13][CH3:14].Cl.CN>C(Cl)Cl>[CH3:1][NH:4][C:23]([C:18]12[CH2:21][CH2:22][C:15]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])([CH2:20][CH2:19]1)[CH2:16][CH2:17]2)=[O:25]N,N-Diisopropylethylamine (1.44 mL, 11.1 mmol) was added to a mixture of 4-pentylbicyclo[2.2.2]octane-1-carboxylic acid (3-A) (1.09 g, 4.45 mmol) and methylamine hydrochloride (1.5 g, 22.3 mmol) in methylene chloride (10 mL) was added and the mixture stirred at room temperature for 18 h. After diluting with methylene chloride, the mixture was washed with water, brine, dried (MgSO4) and concentrated in vacuo to give N-methyl-4-pentylbicyclo[2.2.2]octane-1-carboxamide (3-C). 1H NMR (500 MHz, CDCl3): δ 0.91 (t, 3H); 1.22 (m, 8H); 1.43 (m, 6H); 1.77 (m, 6H); 2.82 (d, 3H) ppm.
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