Hydrochloric Acid → Ethyl 10-amino-3-hydroxy-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxylate

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Reaction Steps

To a mixture of ethyl 10-(((benzyloxy)carbonyl)amino)-3-hydroxy-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxylate (2 g, 4.68 mmol) in ethanol (75 mL) was added 1N HCl (5.15 mL, 5.15 mmol) followed by Pd/C (0.498 g, 0.468 mmol) and the mixture stirred under 1 atm of hydrogen for 18 h. The mixture was then filtered through a pad of CELITE® and the pad washed with dichloromethane. The filtrate was then concentrated to afford the title compound (1.4 g, 91% yield) as an off-white solid. 1H NMR (500 MHz, DMSO-d6) δ: 10.5 (1 H, brs), 4.3 (2 H, q, J=7.02 Hz), 4.0 (2 H, d, J=3.66 Hz), 2.4 (1 H, brs), 2.0-2.1 (4 H, m), 1.8-1.9 (2 H, m), 1.7-1.8 (2 H, m), 1.3 (3 H, t, J=7.02 Hz). LCMS (M+H)=294.32.

Provenance & Evidence