m-Chloroperbenzoic acid → HCID 14677686, compound

Participants

Reaction Steps

The compound of Example 6, (700 mg, 3.0 mmoles) was taken up in about 15 ml CH2Cl2 and cooled to 0° under N2. m-Chloroperbenzoic acid (m-CPBA) was added (660 mg) to the solution and the reaction mixture was stirred 1 hour at 0°. Additional m-CPBA (70 mg) was added and the reaction mixture was stirred for 21 hours at room temperature. Ca(OH)2 (650 mg) was added and the reaction mixture was stirred for 10 minutes then filtered through Celite and concentrated. The residue was taken up in ethyl acetate (10 ml) with Et3N (2 ml) and stirred at room temperature overnight. The concentrate was then concentrated to dryness. Chromatography of the residue on silica gel using ethyl acetate gave the title compound. NMR (90 MHz) (CDCl3) (ppm): 2.5-3.1 (2H, br), 3.20 (2H, d), 3.50 (2H, s), 3.65 (3H, s), 3.6-4.0 (3H, m), 4.70 (1H, m), 6.67 (1H, d), 6.8-7.1 (2H, m).

Provenance & Evidence