m-Chloroperbenzoic acid → HCID 86664590, compound

Participants

Reaction Steps

By a method similar to that used in Example 1, (S)—N-(isoquinolin-3-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (108 mg, 0.350 mmol) and 3-chlorobenzoperoxoic acid (72.5 mg, 0.420 mmol) gave (R)-2-(isoquinolin-3-ylamino)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octane]1′-oxide (95 mg, 83% yield). 1H NMR (500 MHz, MeOD) δ ppm 9.04 (1H, s), 7.97 (1H, d, J=8.24 Hz), 7.76 (1H, d, J=8.24 Hz), 7.61-7.67 (1H, m), 7.44-7.49 (2H, m), 4.03 (1H, d, J=10.99 Hz), 3.87 (1H, d, J=10.99 Hz), 3.65-3.77 (2H, m), 3.44-3.53 (3H, m), 3.27-3.31 (1H, m), 2.43-2.55 (1H, m), 2.32 (1H, br. s.), 2.04-2.22 (3H, m). LCMS: RT=0.54 min, MH+=325.2 [ Waters Acquity SDS: 2 to 98% B, 1 min gradient; hold 98% B, 0.5 min; flow rate 0.8 mL/min; Solvent A: 100% H2O/0.05% TFA; Solvent B: 100% ACN/0.05% TFA].

Provenance & Evidence