Sodium Hydroxide → 5-(4-(tert-Butoxycarbonyl)piperazin-1-yl)picolinic acid

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Reaction Conditions

Reaction Steps

A mixture of tert-butyl 4-(6-(methoxycarbonyl)pyridin-3-yl)piperazine-1-carboxylate 49-3 (1.93 g, 6.01 mmol) and NaOH (530 mg, 13.26 mmol) in dioxane (15 mL) and H2O (15 mL) was stirred at 80° C. for 2 hours. Dioxane was removed by rotary evaporation and the resulting solution was acidified to pH around 4 by 1N HCl aqueous solution, followed by extraction with ethyl acetate (60 mL×3). The combined organic layers were washed with H2O and brine, dried over Na2SO4, and concentrated to dryness by rotary evaporation to afford 5-(4-(tert-butoxycarbonyl)piperazin-1-yl)picolinic acid 49-4 as a yellow solid. MS m/z 308.1 (M+1)

Provenance & Evidence