N-bromobutanimide → HCID 58293817, compound

Participants

Reaction Steps

To a solution of Compound 1059 (810 mg; 2.89 mmol) in 15 mL of acetonitrile was added NBS portionwise (505 mg; 2.83 mmol). The reaction mixture was stirred at room temperature for 10 minutes, quenched with saturated Na2SO3 solution, and extracted with EtOAc (3×). The combined organics were dried (Na2SO4), filtered, and concentrated in vacuo to give a crude light yellow semi-solid. The residue was purified by medium pressure silica gel chromatography, eluting with 0-20% EtOAc/hexanes over 25 minutes, to give tert-butyl 4-(5-bromo-2-methylthiophen-3-yl)piperidine-1-carboxylate (Compound 1060, 590 mg, 57%); 1H NMR (CDCl3): δ 6.7 (s, 1H), 4.2 (m, 2H), 2.6 (m, 3H), 2.2 (s, 3H), 1.6 (m, 2H), 1.5 (m, 2H), 1.45 (s, 9H).

Provenance & Evidence