Potassium Cyanide → Tert-butyl 2,4-dioxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate

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Reaction Conditions

Reaction Steps

A solution of tert-butyl 4-oxopiperidine-1-carboxylate (2.15 g, 10.8 mmol), in 1:1 ethanol/H2O (24 mL), was treated with ammonium carbonate (1.95 g, 21.2 mmol) followed by potassium cyanide (1.30 g, 20 mmol). The mixture was stirred at 60° C. for 2 hours, cooled to room temperature, filtered, and washed sequentially with water, ethanol, and diethyl ether to provide the desired product as a white crystalline solid (1.54 g, 53% yield). 1H NMR (300 MHz, DMSO-d6) δ 10.71 (1H, s), 8.51 (1H, s), 3.80 (2H, d, J=13.5 Hz), 3.09 (2H, br s), 1.66 (2H, td, J=12.2, 4.3 Hz), 1.53–1.46 (2H, m), 1.39 (9H, s). LCMS (2M+H) calcd. for C12H20N3O4: 539.28; found 539.41.

Provenance & Evidence