m-Chloroperbenzoic acid → HCID 54674388, compound

Participants

Reaction Steps

To a solution of (R)-N-(1-cyclohexylethyl)-6-methylnicotinamide (2.28 g, 9.3 mmol prepared from the starting 6-methylnicotinic acid) in CHCl3 was added MCPBA (2.24 g, 1.4 eq) and stirred for 2 h at rt. Saturated aqueous NaHCO3 was added and the organics extracted with CH2Cl2, dried over Na2SO4 and concentrated under reduced vacuum. The residue was dissolved in a minimal amount of acetic anhydride and heated to 125° C. for 40 min. The crude mixture was cooled to rt and aqueous NaHCO3 added. The mixture was extracted with EtOAc, dried over Na2SO4, filtered and concentrated under vacuum. The resulting residue was stirred in MeOH (15 mL) and K2CO3 (1 g) for 2 h, concentrated under reduced pressure and partitioned between EtOAc and H2O, Solvent removal and purification by column chromatography (silica gel) using 30-100% EtOAc/hexanes afforded 3.2a as a white solid (920 mg, 38%): 1H-NMR (400 MHz, CDCl3) δ 8.91 (s, 1H), 8.13 (dd, J1=8.0 Hz, J2=2.0 Hz, 1H), 7.36 (d, J=8.0 Hz, 1 H), 5.96 (d, J=8.0 Hz, 1H), 4.84 (s, 2H), 4.15-4.08 (m, 1 H), 1.85-1.04 (m, 14 H)); LC-MS (220 nm), >98%, 263.2 [M+H].

Provenance & Evidence