Pyridine-3-amine (143 mg, 1.52 mmol) was added to a solution of 1-azatricyclo[3.3.1.13,7]decan-4-one (151 mg, 1.00 mmol) in acetic acid (5 mL). Anhydrous sodium sulfate (1.82 g, 12.8 mmol) was added, and the mixture was stirred at room temperature. After 10 minutes, sodium triacetoxyborohydride (412 mg, 1.94 mmol) was added and the mixture was stirred at room temperature for 10 hours. The reaction mixture was filtered through diatomaceous earth with a chloroform (5 mL) rinse. The filtrate was concentrated under vacuum, and the residue was purified by flash chromatography on silica (eluted with chloroform-methanol-concentrated ammonium hydroxide, 90:10:1) to provide a colorless gum. This was combined with 4-methylbenzenesulfonic acid monohydrate (29 mg) in a boiling mixture of ethyl acetate (5 mL) and EtOH (0.5 mL) and cooled to room temperature. After 30 hours, the product was collected by filtration, washed with ethyl acetate (2 mL) and dried under vacuum to provide the titled compound: 1H NMR (300 MHz, methanol-D4) δ 1.91-2.00 (m, 3H), 2.14-2.33 (m, 5H), 2.36 (s, 6H), 3.57 (s, 2H), 3.69 (s, 4H), 4.03 (s, 1H), 7.23 (d, J=7.9 Hz, 4H), 7.70 (d, J=8.3 Hz, 4H), 7.72-7.77 (m, 1H), 7.81-7.87 (m, 1H), 8.01 (d, J=5.6 Hz, 1H), 8.18 ppm (d, J=2.8 Hz, 1H): MS (DCI/NH3) m/z 230 (M+H)+; Anal. Calcd for C14H19N3.2C7H8O3S.0.5H2O: C, 57.71; H, 6.23; N, 7.21. Found: C, 57.78; H, 6.03; N, 7.19.
