Methyl iodide → 4-[(6-chloropyridin-3-yl)methyl]-7a-methyl-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one

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Reaction Conditions

Reaction Steps

43 mg (0.16 mmol) of 4-[(6-chloropyridin-3-yl)methyl]-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one (1-2) are dissolved in 2.5 ml of tetrahydrofuran, the mixture is cooled to −78° C. and 96 μl (0.16 mmol) of a 1.7M solution of tert-butyllithium in pentane are added. After 30 minutes of stirring at −78° C., 15 μl (0.24 mmol) of methyl iodide are added, and the mixture is stirred at −78° C. for a further 30 min, warmed to room temperature and stirred at room temperature for a further 3 hours. Concentration under reduced pressure and purification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm) using the mobile phase ethyl acetate gives 16 mg (35% of theory) of 4-[(6-chloropyridin-3-yl)methyl]-7a-methyl-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one.

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