m-Chloroperbenzoic acid → HCID 54588500, compound

Participants

Reaction Steps

To (R)—N-(1-Fluoroisoquinolin-3-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (0.063 g, 0.193 mmol) in CHCl3 (15 mL) was added m-CPBA (0.034 g, 0.195 mmol) at room temperature. The reaction was 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-(1-fluoroisoquinolin-3-ylamino)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octane]1′-oxide (0.050 g, 0.146 mmol, 76% yield) as a white powder. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.12-8.42 (m, 1H), 8.01 (d, J=8.2 Hz, 1H), 7.86 (br. s., 1H), 7.73 (br. s., 1H), 7.43-7.60 (m, 1H), 6.93-7.35 (m, 1H), 3.69-4.05 (m, 1H), 3.58 (br. s., 1H), 3.00-3.33 (m, 6H), 2.19 (br. s., 2H), 1.94 (d, J=10.1 Hz, 3H). LC/MS: retention time 1.78 (M+1=343.1).

Provenance & Evidence