m-Chloroperbenzoic acid → HCID 54588461, compound

Participants

Reaction Steps

(R)—N-(5-Phenylthiazol-2-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (0.101 g, 0.297 mmol) was dissolved in THF (15 mL) and treated with m-CPBA (0.061 g, 0.356 mmol) for 30 min. at room temperature. The reaction was concentrated in vacuo to afford the crude product. The crude product was purified by reverse phase HPLC to yield pure fractions. The fractions were concentrated via vacuo and dried in a vac. oven for 18 hours to yield (S)-2-(5-phenylthiazol-2-ylamino)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octane]1′-oxide (0.03 g, 0.082 mmol, 27.8% yield) as a white powder. 1H NMR (500 MHz, DMSO-d6) δ ppm 7.86-8.12 (m, 1H), 7.64 (br. s., 2H), 7.44 (s, 3H), 4.13-4.31 (m, 3H), 3.97-4.07 (m, 1H), 3.90 (d, J=10.7 Hz, 4H), 3.54-3.74 (m, 1H), 2.28-2.42 (m, 1H), 1.95-2.24 (m, 3H). LC/MS: retention time 1.04 (M+1=357.1).

Provenance & Evidence