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 eq) and N-ethyl-diisopropylamine (41.608 mmol, 4 eq) were dissolved in 2-propanol (20 ml). 4-Chloropyridine (31.206 mmol, 3 eq) was added and the mixture was heated at 90° C. for 16 h. Saturated sodium bicarbonate solution (50 ml) was added and the phases were separated. The aqueous phase was extracted with ethyl acetate (4×50 ml) and the combined org. phases were washed with saturated sodium chloride solution (50 ml), dried over magnesium sulfate and concentrated. After purification by column chromatography (silica gel, ethyl acetate/methylene chloride/methanol/ammonia (25% aq) (100:100:25:1), the desired product was obtained as a yellow oil. Yield: 1.8 g (55%)

Provenance & Evidence