(1R,4R)-2-[(4-methylphenyl)sulfonyl]-5-(3-pyridinylmethyl)-2,5-diazabicyclo[2.2.1]heptane → (1R,4R)-2-(3-pyridinylmethyl)-2,5-diazabicyclo[2.2.1]heptane trihydrobromide

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Reaction Steps

The product from Example 20A (320 mg, 0.9 mmol) in acetic acid (3.4 mL) and 33% HBr/acetic acid (7 mL) was heated to 70° C. for 18 hours. After cooling to ambient temperature, the precipitate was filtered, washed with ether, and dried. The resulting solids were recrystallized from EtOH/EtOAc to provide the title compound (332 mg, 80%). 1H NMR (DMSO-d6, 300 MHz) δ 2.22 (m, 1H), 2.47 (m, 1H), 3.29-3.48 (m, 2H), 3.35 (m, 1H), 3.69 (m, 1H), 4.19-4.53 (m, 2H), 5.59 (m, 2H), 8.05 (m, 1H), 8.62 (m, 1H), 8.78-8.88 (m, 2H); MS (DCI/NH3) m/z 190 (M+H)+; Anal. Calcd. for C11H15N3.3.0 HBr.0.1H2O: C, 30.46; H, 4.23; N, 9.69. Found: C, 30.83; H, 4.25; N, 9.30.

Provenance & Evidence