Triacetoxyperiodinane → 6-Benzyloxycarbonylamino-8-oxo-5,6,7,8-tetrahydroquinoline

Participants

Reaction Steps

To a stirred solution of 6-benzyloxycarbonylamino-8-hydroxy-5,6,7,8-tetrahydroquinoline, cis-trans mixture (1.02 g, 3.42 mmol) in methylene chloride (34 mL) at room temperature under nitrogen was added Dess-Martin periodinane (1.73 g, 4.45 mmol). After 2 h, the reaction mixture was diluted with ethyl acetate. The organic layer was washed sequentially with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, and evaporated under vacuum to yield a residue. The residue was purified by reverse phase preparative HPLC to obtain the title compound (319 mg, 31%) as a brown oil. 13C NMR (400 MHz, CDCl3) δ 194.1, 155.4, 149.8, 147.6, 138.3, 137.2, 136.0, 128.6, 128.3, 128.2, 127.5, 67.0, 46.7, 45.4, 35.4. 1H NMR (400 MHz, CDCl3) δ 8.66 (d, J=4.4 Hz, 1H), 7.61 (d, J=7.9 Hz, 1H), 7.36 (dd, J=4.4, 7.9 Hz, 1H), 7.26 (m, 5H), 5.02 (s, 2H), 4.34 (s, 1H), 3.29 (d, J=15.4 Hz, 1H), 3.04 (d, J=4.0 Hz, 1H), 2.99 (d, J=4.0 Hz, 1H), 2.80 (dd, J=9.2, 11.4 Hz, 1H). HPLC/MS [M+H]+, 297.

Provenance & Evidence