Iodoethane → HCID 86680454, compound

Participants

Reaction Conditions

Reaction Steps

To (7R,8aS)-2-{[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}octahydropyrrolo[1,2-a]pyrazin-7-ol (0.3 mmol, Example 187) in tetrahydrofuran (1 mL) at room temperature was added NaH (20 mg, 60% in mineral oil). After 15 minutes, iodoethane (0.39 mmol) was added. The mixture was stirred at 60° C. for 2 days. The mixture was partially purified by chromatography on silica gel (CH2Cl2/CH3OH=10:1) to give the title compound as an impure solid (77 mg). The product was purified by HPLC (Gilson®, Xbridge™ 30×100 mm column, eluted with pH=10 aqueous ammonium bicarbonate-ammonium hydroxide/methanol (70:30 to 0:100 gradient over 16 minutes), flow rate 36 mL/minute, UV=220 nm) to give the title compound (20 mg, 16% yield) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.07 (m, 3H), 1.47 (m, 1H), 1.73 (m, 1H), 2.00 (m, 1H), 2.08 (m, 1H), 2.19 (m, 1H), 2.39 (m, 6H), 2.93 (m, 1H), 3.63 (m, 1H), 3.76 (m, 1H), 3.92 (m, 1H), 8.04 (m, 3H); MS (ESI) m/z 469 (M+H)+.

Provenance & Evidence