m-Chloroperbenzoic acid → HCID 54588457, compound

Participants

Reaction Steps

mCPBA (0.074 g, 0.332 mmol) was added to a suspension of (R)—N-(5-m-tolylpyrimidin-2-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (0.116 g, 0.332 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-m-tolylpyrimidin-2-ylamino)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octane]1′-oxide as an off-white solid (0.067 g, 0.176 mmol, 53%). 1H NMR (400 MHz, MeOD) δ ppm 8.79 (2H, s), 7.27-7.49 (3H, m), 7.20 (1H, d, J=7.55 Hz), 4.03 (1H, d, J=10.32 Hz), 3.88 (1H, d, J=10.58 Hz), 3.59-3.77 (2H, m), 3.38-3.52 (3H, m), 3.21-3.28 (1H, m), 2.40-2.52 (1H, m), 2.28-2.35 (1H, m), 1.96-2.21 (3H, m). LC/MS RT=1.71; [M+H]+=366.34.

Provenance & Evidence