Triethylamine → HCID 59261033, compound

Participants

Reaction Steps

A cooled (0° C.) solution of tert-butyl 4-(3-hydroxyisoxazol-5-yl)piperidine-1-carboxylate (493 mg, 1.84 mmol) in 5 mL of THF was treated with toluenesulfonyl chloride (386 mg, 2.02 mmol) followed by triethylamine (295 μL, 2.12 mmol). The resulting mixture was warmed to rt and stirred for 2 h. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified by MPLC (silica, 50% ethyl acetate/hexanes) to furnish tert-butyl 4-(3-{[(4-methylphenyl)sulfonyl]oxy}isoxazol-5-yl)piperidine-1-carboxylate. 1H NMR (500 MHz, CDCl3) δ 7.87 (d, J=8.5 Hz, 2H), 7.39 (d, J=8.0 Hz, 2H), 6.06 (s, 1H), 4.15 (br m, 2H), 2.88 (m, 3H), 2.49 (s, 3H), 2.00 (dd, J=13, 2.5 Hz, 2H), 1.62 (dq, J=4.5, 12.5 Hz, 2H), 1.49 (s, 9H).

Provenance & Evidence