Piperidine → Methyl 3-(1-(2-acetylaminoethyl)-2,5-dimethylpyrrol-3-yl)-2propenoate

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Reaction Steps

6.1 g (0.05 mol) of monomethyl malonate are dissolved in 20 ml of pyridine. After addition of 10.4 g (0.05 mol) of 1-(2-acetylaminoethyl)-2,5-dimethylpyrrole-3-aldehyde (see Example 13) and 1 ml of piperidine, the mixture is heated under reflux for 15 hours. After addition of a further 27 g of monomethyl malonate, heating is continued for a further 24 hours, the mixture is concentrated, the residue is taken up in water, the mixture is extracted with methylene chloride and the methylene chloride phase is washed with dilute acid and alkali and concentrated. Column chromatography with methylene chloride:methanol=98:2 as the mobile phase gives 7.5 g of product, which can be recrystallized from ethyl acetate.

Provenance & Evidence