Hydrogen Peroxide → HCID 58993659, compound

Participants

Reaction Steps

tert-Butyl 4-(((5-bromo-4′-fluorobiphenyl-3-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (0.47 g, 0.85 mmol) was dissolved in dry tetrahydrofuran (5 mL) and stirred at room temperature for 15 min. The stirred mixture was cooled to −78° C. and treated with a solution of n-butyllithium (1.6 M in hexanes, 0.61 mL, 0.98 mmol) over several minutes. After 30 min, the mixture was treated with trimethylborate (0.28 mL, 2.55 mmol). The reaction mixture was stirred at 78° C. for 1 h, then allowed to warm to room temperature over several hours. The mixture was cooled to 0° C. and treated with a 10 N sodium hydroxide solution (60 μL) and hydrogen peroxide (30% in water, 0.44 mL, 3.9 mmol). The reaction was warmed to room temperature over several hours and then treated with saturated ammonium chloride. The reaction was diluted with ethyl acetate. The layers were separated and the organic layer washed with brine (2×), dried over sodium sulfate, filtered, and concentrated. Flash chromatography on silica gel (30% ethyl acetate/hexanes) afforded 280 mg (67%). 1H-NMR (CDCl3, 500 MHz) δ 7.38-7.43 (m, 2H), 7.19-7.35 (m, 5H), 7.02-7.09 (m, 2H), 6.86-6.88 (m, 1H), 6.79 (s, 1H), 6.46 (s, 1H), 4.33 (s, 2H), 3.70-3.74 (m, 2H), 3.38 (s, 2H), 2.98-3.07 (m, 2H), 2.13-2.17 (m, 2H), 1.83-1.92 (m, 2H), 1.41 (s, 9H). Mass spec.: 492.41 (MH)+.

Provenance & Evidence