m-Chloroperbenzoic acid → HCID 54588499, compound

Participants

Reaction Steps

(R)—N-(6-Fluoro-3,4′-bipyridin-2′-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (0.11 g, 0.311 mmol) in THF (10 mL) was treated with m-CPBA (0.059 g, 0.342 mmol) and stirred at room temperature for 2 hours. Reaction was complete by TLC and the product was purified by chromatography (Biotage: 5-20% of 8:2 MeOH:NH4OH in CHCl3) and the pure fractions were combined to yield (S)-2-(6-fluoro-3,4′-bipyridin-2′-ylamino)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octane]1′-oxide (0.05 g, 0.134 mmol, 43.1% yield) as a yellow powder. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.11 (br. s., 1H), 8.64 (br. s., 1H), 8.21-8.43 (m, 2H), 7.04-7.44 (m, 3H), 3.77 (d, J=10.1 Hz, 2H), 2.98-3.65 (m, 6H), 2.18 (br. s., 2H), 1.74-2.01 (m, 3H). LC/MS: retention time 0.78 (M+1=370.2).

Provenance & Evidence