Sodium Methoxide → N-Methyl-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline

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A solution of N-methyl-4a-(m-methoxyphenyl)-1,3-diketo-trans-decahydroisoquinoline (4.6 g, 1.6 mmole) and sodium methoxide (1.84 g, 3.4 mmole) in 150 ml of methanol was stirred at room temperature under nitrogen for 20 hours. It was poured into 150 ml of ice-water and extracted with ether, and the combined extracts were washed with 3 N hydrochloric acid and sat. sodium bicarbonate, dried (Na2SO4) and evaporated. The crude product was a white viscous oil (3.8 g). Thin layer chromatography on silica gel, eluting with 10% ether/benzene, showed a major spot (Rf 0.31) and a minor component (Rf 0.07). The major component, N-methyl-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline, was clearly separated by preparative thick layer chromatography and isolated as a colorless oil.

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