Pyridine → Tert-butyl(1-(4-(5-(methoxyimino)-3-phenyl-5,6,7,8-tetrahydroquinolin-2-yl)phenyl)cyclobutyl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl(1-(4-(5-oxo-3-phenyl-5,6,7,8-tetrahydroquinolin-2-yl)phenyl)cyclobutyl)carbamate (90 mg, 0.19 mmol) in anhydrous ethanol (2.0 mL) was added O-methylhydroxylamine hydrochloride (80 mg, 0.96 mmol) and pyridine (80 μL, 0.99 mmol). The resulting yellow solution was heated to 90° C. under a nitrogen atmosphere. The reaction mixture was allowed to cool to room temperature and concentrated to dryness under reduced pressure. The residue was mixed with water (2.0 mL) and extracted into ethyl acetate (3×2.0 mL). The combined organic phases were washed with brine (2×4.0 mL), dried over Na2SO4, filtered and concentrated to dryness under reduced pressure to give a yellow oil. The residue was purified by Biotage chromatography (silica, hexane:ethyl acetate, gradient elution from 95:5 to 60:40) to give the desired product as a white solid (44 mg, 46% yield). 1H-NMR (500 MHz, CD3OD) δ 8.29 (1H, s), 7.35 (2H, d), 7.26-7.32 (5H, m), 7.16-7.21 (2H, m), 4.01 (3H, s), 3.02 (2H, t), 2.83 (2H, t), 2.36-2.52 (4H, m), 2.04-2.16 (1H, m), 2.01 (2H, p), 1.81-1.92 (1H, m), 1.15-1.50 (9H, br m). LCMS (Method A) RT=8.28 min, M+H+=498.10.

Provenance & Evidence