m-Chloroperbenzoic acid → HCID 54588459, compound

Participants

Reaction Steps

A solution of (R)—N-(6-(1H-imidazol-1-yl)pyrimidin-4-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (52.9 mg, 0.163 mmol) and 3-chlorobenzoperoxoic acid (33.7 mg, 0.195 mmol) in 2 mL THF was stirred at room temperature for 24 h. The reaction was concentrated and the crude product was purified by flash chromatography on a 40 g silica gel cartridge with 20 to 40% [9:1 MeOH/NH4OH] in EtOAc, 40 min. Pure fractions were pooled, concentrated, and dried. The residue was dissolved in CDCl3, filtered through a 0.4μ filter, concentrated, and dried under high vacuum to yield (S)-2-(6-(1H-imidazol-1-yl)pyrimidin-4-ylamino)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octane]1′-oxide (53 mg, 95% yield).

Provenance & Evidence