반응 #534451

반응 방정식

mCPBA

(R)—N-(6-(cyclopentyloxy)pyrimidin-4-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine

→

(S)-2-(6-(cyclopentyloxy)pyrimidin-4-ylamino)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octane]1′-oxide

용매

THF

반응 조건

후처리

1. 1
   농축concentrated
2. 2
   기타The residue was purified by silica gel chromatography (5-25% 9:1 methanol:ammonium hydroxide-ethyl acetate)

실험 절차

mCPBA (0.114 g, 0.510 mmol) was added to a solution of (R)—N-(6-(cyclopentyloxy)pyrimidin-4-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (0.175 g, 0.510 mmol) in THF (15 ml). The mixture was stirred at room temperature for 18 h and concentrated. The residue was purified by silica gel chromatography (5-25% 9:1 methanol:ammonium hydroxide-ethyl acetate) to afford (S)-2-(6-(cyclopentyloxy)pyrimidin-4-ylamino)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octane]1′-oxide an off-white solid (0.076 g, 0.207 mmol, 41%). 1H NMR (400 MHz, MeOD) δ ppm 8.38 (1H, s), 6.34 (1H, br. s.), 5.18-5.37 (1H, m), 4.01 (1H, d, J=11.08 Hz), 3.85 (1H, d, J=10.83 Hz), 3.58-3.75 (2H, m), 3.34-3.53 (3H, m), 3.20-3.27 (1H, m), 2.32-2.46 (1H, m), 2.23-2.31 (1H, m), 1.98-2.19 (3H, m), 1.93-1.99 (2H, m), 1.68-1.84 (4H, m), 1.55-1.70 (2H, m).

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