m-Chloroperbenzoic acid → HCID 54588501, compound

Participants

Reaction Steps

To (R)—N-(5-bromo-6-fluoropyridin-2-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (0.064 g, 0.180 mmol) in CHCl3 (15 mL) was added m-CPBA (0.032 g, 0.186 mmol) at room temperature. The reaction stirred at room temperature for 3 hours. TLC showed lower spot and no starting material. The mixture was purified by chromatography (Biotage: 15-20% of 9:1 MeOH:NH4OH in CHCl3; ˜1.1 L) to yield the pure fractions. The fractions were combined and the solvent was removed to yield (S)-2-(5-bromo-6-fluoropyridin-2-ylamino)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octane]1′-oxide (0.045 g, 0.119 mmol, 65.9% yield) as a yellow powder. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.31-8.76 (m, 1H), 8.00 (br. s., 1H), 6.46-6.96 (m, 1H), 3.73 (d, J=11.0 Hz, 2H), 3.56 (br. s., 1H), 3.37 (br. s., 3H), 2.98-3.27 (m, 2H), 2.11 (br. s., 2H), 1.73-2.00 (m, 3H).

Provenance & Evidence