Trimethylsilyl iodide → [3S,4aR,6S,8aR]-Ethyl-6-((4-Ethoxycarbonyl-1H-Imidazol-1-yl)Methyl)-1,2,3,4,4a,5,6,7,8,8a-Decahydroisoquinoline-3-Carboxylate

Participants

Reaction Steps

To a solution of 0.90 g of [3S,4aR,6S,8aR]-ethyl-6-((4-ethoxycarbonyl-1H-imidazol-1-yl)methyl)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate in 20 ml of methylene chloride was added 1.5 ml trimethylsilyl iodide. The reaction was stirred at room temperature for six hours, quenched with excess absolute ethanol and evaporated to dryness. The residue was purified by strong cation exchange chromatography eluting with 10-50% methanol in chloroform followed by 50% 2M ammonia/methanol in chloroform to provide the final title compound, [3S,4aR,6S,8aR]-ethyl-6-((4-ethoxycarbonyl-1H-imidazol-1-yl)methyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate.

Provenance & Evidence