Ethyl 2-(4-hydroxy-3,5-dimethylphenyl)-8,9-dimethoxy-3-methyl-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-1-carboxylate → Ethyl 8-methoxy-9-hydroxy-2-(3,5-dimethyl-4-hydroxyphenyl)-3-methyl-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

1 g (2.3 mmol) of ethyl 2-(4hydroxy-3,5-dimethylphenyl)-8,9-dimethoxy-3-methyl-5,6-dihydropyrrolo[2,1-a]isoquinoline-1-carboxylate (Example 1) was intimately mixed with 4 g of pyridine hydrochloride and heated to fusion at 150° C. The mixture was stirred at 150° C. for 20 min., then cooled to room temperature and dissolved in a mixture of ethyl acetate and dilute hydrochloric acid. The layers were separated, the aqueous layer was extracted with ethyl acetate, and the combined organic phases were washed with water, dried over Na2SO4, and the solvent was evaporated under reduced pressure. Column chromatography on silica gel using a dichloromethane/ethyl acetate 10:1 mixture as eluant afforded the title compounds ethyl 8-methoxy-9-hydroxy-2-(3,5-dimethyl-4-hydroxyphenyl)-3-methyl-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-1-carboxylate (Example 26):

Provenance & Evidence