Water → 7-tert-butoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl adamantanecarboxylate

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Reaction Steps

In 2,000 ml of acetonitrile were dissolved 282 g of tert-butyl 6-hydroxy-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-7-carboxylate (21), 157 g of triethylamine and 13.6 g of 4-dimethylaminopyridine. Below 20° C., 328 g of adamantanecarboxylic chloride (26) was added dropwise to the solution, which was stirred at room temperature for 3 hours. Then 1,000 g of water was added to the solution, followed by standard work-up. Recrystallization from methylene chloride gave 391 g of the target compound (yield 85%).

Provenance & Evidence