Water → 1-Methylethyl 4-[(1S)-1-({5-[2-fluoro-4-(methylsulfonyl)phenyl]-2-pyrazinyl}oxy)ethyl]-1-piperidinecarboxylate

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Reaction Steps

The title compound (0.195 g) was prepared from 1-methylethyl 4-[(1S)-1-({5-[2-fluoro-4-(methylthio)phenyl]-2-pyrazinyl}oxy)ethyl]-1-piperidinecarboxylate (0.33 g, 0.76 mmol) and Oxone® (1.41 g, 2.29 mmol) in acetone (25 mL) and water (10 mL) in a manner similar to Example 166, Step 2. The crude product was purified by chromatography on an ISCO silica gel column using 0 to 50% EtOAc/hexanes, followed by chiral separation on an AS-H column with 25% MeOH in CO2, 140 bar, 40° C. at 2 mL/min. The first eluting peak was further purified by trituration with 9% EtOAc/hexanes to afford the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.64 (s, 1H), 8.27 (s, 1H), 8.20 (t, 1H, J=7.8 Hz), 7.85-7.70 (m, 2H), 5.20-5.10 (m, 1H), 4.89 (septet, 1H, J=6.2 Hz), 4.30-4.15 (m, 2H), 3.09 (s, 3H), 2.80-2.65 (m, 2H), 1.90-1.65 (m, 3H), 1.40-1.15 (m, 11H); LRMS (ESI), m/z 466 (M+H).

Provenance & Evidence