m-Chloroperbenzoic acid → HCID 54588456, compound

Participants

Reaction Steps

mCPBA (0.060 g, 0.266 mmol) was added to a suspension of (R)—N-(5-bromo-4-phenylpyrimidin-2-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (0.1 g, 0.241 mmol) in THF (10 ml). The mixture was stirred at room temperature for 18 h, concentrated, and purified by silica gel chromatography (5-25% 9:1 methanol:ammonium hydroxide-ethyl acetate) to afford (S)-2-(5-bromo-4-phenylpyrimidin-2-ylamino)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octane]1′-oxide as an off-white solid (0.066 g, 0.149 mmol, 62%). 1H NMR (400 MHz, MeOD) δ ppm 8.72 (1H, s), 7.74 (2H, dd, J=6.92, 2.64 Hz), 7.39-7.53 (3H, m), 4.01 (1H, d, J=10.58 Hz), 3.85 (1H, d, J=10.32 Hz), 3.61-3.74 (2H, m), 3.37-3.50 (3H, m), 3.19-3.26 (1H, m), 2.37-2.51 (1H, m), 2.26-2.33 (1H, m), 1.95-2.20 (3H, m). LC/MS RT=1.78; [M+2]+=432.19.

Provenance & Evidence