Hydrogen Peroxide → HCID 59177814, compound

Participants

Reaction Steps

A mixture of 1-methylethyl 4-[({6-[2-fluoro-4-(methylthio)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate (50 mg, 0.12 mmol) in 1,1,1,3,3,3-hexafluoro-2-propanol (2 mL) was treated with 30% aqueous H2O2 (0.027 mL, 0.24 mmol) at ambient temperature. After 2 h, saturated aqueous Na2SO3 (5 mL) was added carefully and the mixture was stirred for 10 min. EtOAc (3 mL) was added, the organic layer was separated and dried over Na2SO4 and the solvent evaporated off. The crude product was purified by reverse-phase preparative HPLC using a CH3CN:H2O gradient (10:90 to 100:0) with 0.1% TFA as a modifier to give 25 mg (48%) of the title compound as a white solid. 1HNMR (400 MHz, CDCl3): δ 8.41 (d, 1H, J=2.7 Hz), 8.14 (t, 1H, J=7.8 Hz), 7.78 (dd, 1H, Ja=8.7 Hz, Jb=1.5 Hz), 7.51 (dd, 1H, Ja=10.5 Hz, Jb=1.4 Hz), 7.44 (dd, 1H, Ja=8.2 Hz, Jb=1.5 Hz), 7.30-7.23 (m, 1H), 4.92 (septet, 1H, J=6.2 Hz), 4.30-4.15 (m, 2H), 3.90 (d, 2H, J=6.4 Hz), 2.85-2.74 (m, 2H), 2.76 (s, 3H), 2.06-1.96 (m, 1H), 1.85 (m, 2H), 1.88-1.22 (m, 2H), 1.24 (d, 6H, J=6.4 Hz); LRMS (ESI), m/z 435 (M+H).

Provenance & Evidence