m-Chloroperbenzoic acid → (S)-2-(5-chloro-4-methylpyridin-2-ylamino)-4H-1'-azaspiro[oxazole-5,3'-bicyclo[2.2.2]octane]1'-oxide

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Reaction Steps

To (R)—N-(5-Chloro-4-methylpyridin-2-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (0.04 g, 0.13 mmol) in THF (10 mL) was added m-CPBA (0.025 g, 0.14 mmol). The reaction stirred at room temperature for 2 hours and was then concentrated to a crude powder. The product was purified by chromatography (Biotage: 85% CHCl3, 14% MeOH, 1% NH4OH) to yield (S)-2-(5-chloro-4-methylpyridin-2-ylamino)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octane]1′-oxide (0.019 g, 0.06 mmol, 44% yield) as a white powder. 1H NMR (500 MHz, MeOD) δ ppm 8.18 (s, 1H), 6.75-7.09 (m, 1H), 4.00 (d, J=10.4 Hz, 1H), 3.84 (d, J=10.4 Hz, 1H), 3.61-3.78 (m, 2H), 3.41-3.54 (m, 3H), 3.23-3.38 (m, 3H), 2.45 (br. s., 1H), 2.25-2.38 (m, 4H), 1.88-2.22 (m, 1H). MS (LC/MS) R.T.=0.91; [M+H]+=323.11.

Provenance & Evidence