Methanol → Methyl-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-yl]-acetate

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Reaction Steps

g 1) 25.76 g (1060 mmol) of magnesium shavings were added to a solution of 35.33 g (106 mmol) of methyl (E)-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-ylidene]acetate in 850 ml of methanol and the mixture was stirred at room temperature for 2 hours. The solution was filtered over Dicalite and evaporated. The residue was partitioned between 300 ml of methylene chloride and 500 ml of saturated ammonium chloride solution. The aqueous phase was extracted three times with 250 ml of methylene chloride. The organic phase was dried (Na2SO4), filtered and evaporated. Chromatography (silica gel, ethyl acetate/methanol/NH4OH 200:10:1) yielded 7.16 g (20%) of methyl cis-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-yl]-acetate as a colorless oil, Rf=0.23 ((silica gel, ethyl acetate/methanol/NH4OH 200:10:1) and 23.51 g (66%) of methyl-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-yl]-acetate as a colorless oil, Rf=0.12 (silica gel, ethyl acetatelmethanol/NH4OH 200:10:1).

Provenance & Evidence