Dichloromethane → 2,5-Di(4-pyridyl)-4-methylthiophen-3-ylmethylhydroxylamine trihydrochloride

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Reaction Steps

To a stirred solution of N,O-di-tert-butoxycarbonyl-[2,5-di(4-pyridyl)-4-methylthiophen-3-yl]methylhydroxylamine (0.16 g) in CH2Cl2 (15 mL) was added trifluoroacetic acid (0.5 mL) and the mixture watered for 2 hours at room temperature. Trifluoroacetic acid (3 mL) was additionally added to the reaction mixture, and stirred for 2 hours. Saturated aqueous NaHCO3 solution was added to the reaction mixture and the whole was extracted with CH2Cl2 (100 mL×2). The combined organic layers were washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate-CH2Cl2 (1:1). The crude product was dissolved in 10% methanolic HCl (1 mL) and the volatiles were removed by evaporation. The resulting solid was recrystallized from diisopropyl ether to give the title compound (0.031 g).

Provenance & Evidence