Tert-butyl 4-(2-ethoxy-2-oxoethyl)-4-(nitromethyl)piperidine-1-carboxylate → Tert-butyl 3-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

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Reaction Steps

A mixture of tert-butyl 4-(2-ethoxy-2-oxoethyl)-4-(nitromethyl)piperidine-1-carboxylate (330 g, 990 mmol, 1.00 equiv, 99%) and Ni (40 g, 0.15 equiv) in ethanol (1200 mL) was stirred for 24 h under a hydrogen atmosphere at room temperature. The solid was filtered out. The filtrate was concentrated under vacuum. The crude product was purified by re-crystallization from ether to afford the title compound. LC-MS (ES, m/z): 199 [M+H]+; 1H-NMR (400 MHz, CDCl3, ppm): 1.447-1.476(9H, s), 1.597-1.673(4H, m, J=30.4 Hz), 2.235(2H, s), 3.226(2H, s), 3.284-3.348(2H, m, J=25.6 Hz), 3.507-3.567(2H, m, J=24 Hz), 6.048(1H, s).

Provenance & Evidence