Tetrahydrofuran → 4-oxoadamantane-1-carboxamide

Participants

Reaction Steps

50 g of 4-oxoadamantane-1-carboxylic acid (1) was dissolved in 300 mL of MC and to the resulting solution was slowly added dropwise 30 mL of oxalic chloride. Then, five drops of DMF were added and the resulting mixture was stirred at room temperature for two hours, distilled under a reduced pressure, and then vacuum-dried. The compound as vacuum-dried was dissolved in 150 mL of anhydrous THF and the resulting solution was added dropwise to a solution prepared by mixing 60 mL of ammonia water and 150 mL of THF. This reaction was extremely exothermic and thus the reactor cooled with iced water. After being stirred for 30 minutes, solids in the reaction product were filtered off by using MC, and the organic solution being collected was dried over MgSO4 and then filtered and dried under a reduced pressure. The resulting product was recrystallized with a solution of MeOH and ether to provide 43 g of 4-oxoadamantane-1-carboxamide (2).

Provenance & Evidence