Water → HCID 42641721, compound

Participants

Reaction Steps

To a solution of Example 1 (0.5 g, 1.65 mmol) in dichloromethane (4.8 mL) was added triethylamine (0.46 mL, 3.30 mmol) and methyl 4-bromobutyrate (0.24 mL, 1.90 mmol). The resulting solution was stirred at ambient temperature for 16 hours. Water (25 mL) and dichloromethane (25 mL) were added to the reaction mixture and the crude residue was extracted into dichloromethane. The organic portion was washed with water (25 mL), washed with brine (25 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by silica gel flash chromatography using hexane/EtOAc (gradient system) to give the title compound (0.15 g, 24%); 1H NMR (400 MHz, CDCl3); δ 1.66-1.86 (m, 5H), 1.96 (m, 1H), 2.20-2.45 (m, 4H), 2.86 (m, 2H), 3.14 (m, 1H), 3.63 (s, 3H), 3.74 (m, 1H), 3.89 (m, 1H), 3.92 (s, 2H), 6.82 (d, J=8.4 Hz, 2H), 7.08 (d, J=8.0 Hz, 2H), 7.16-7.20 (m, 3H), 7.27 (m, 2H); MS (m/z) 368.4 (M+1); LC (90.6%).

Provenance & Evidence