Sodium hydride → [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

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Reaction Steps

Ethyl-4-imidazolecarboxylate (486 mg, 3.46 mmol) was added in portions to a slurry of sodium hydride (146 mg of a 60% mineral oil dispersion, 3.64 mmol) in THF (3.0 mL). The resulting tea-colored solution was stirred at room temperature for 55 minutes. It was then treated with [3S,4aR,6S,8aR]-ethyl-6-((3-nitrophenylsulfonyloxy)methyl)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate (1.68 g, 3.46 mmol, prepared in example 1) dissolved in THF (3.5 mL), and the reaction mixture was stirred overnight at room temperature. The reaction was then partitioned between dichloromethane (6.5 mL) and water (6.5 mL), and the layers were separated. The aqueous layer was extracted with dichloromethane (5 mL). The organic extract and organic layer were combined, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to provide the crude title compound. This material was purified flash chromatography (5% to 10% ethanol/toluene containing 0.5% dimethylamine, 34 g silica gel) to provide the purified intermediate title compound (1.16 g, 79%) as a colorless film.

Provenance & Evidence