4-Chloropyridine → tert-Butyl 8-(pyridin-4-yl)-2,8-diazaspiro[4,5]decane-2-carboxylate

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Reaction Conditions

Reaction Steps

tert-Butyl-2,8-diazaspiro[4.5]decane-2-carboxylate (10.403 mmol, 1 equiv.) and N-ethyl-diisopropylamine (41.608 mmol, 4 equiv.) were placed in 2-propanol (20 ml). 4-Chloropyridine (31.206 mmol, 3 equiv.) was added, and the mixture was heated for 16 hours at 90° C. Saturated sodium hydrogen carbonate solution (50 ml) was then added, and the phases were separated. The aqueous phase was extracted with ethyl acetate (4×50 ml), and the combined organic phases were washed with saturated NaCl solution (50 ml) and dried over magnesium sulfate. After purification by column chromatography (ethyl acetate/DCM/methanol/ammonia (25% aq), 100:100:25:1), the desired product was obtained in the form of a yellow oil. Yield: 1.8 g (55%)

Provenance & Evidence