Perchloric Acid → t-butyl octahydro-3-oxo-1H-isoindole-1-carboxylate

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Reaction Steps

The intermediate t-butyl octahydro-3-oxo-1H-isoindole-1-carboxylate is prepared from octahydro-3-oxo-1H-isoindole-carboxylic acid (Example 5) as follows. A mixture of 10 g of this acid and 0.4 ml of 70% perchloric acid in 150 ml of t-butyl acetate is allowed to stand for 2.5 days. An additional 50 ml of t-butyl acetate is added and the reaction is allowed to continue for 15 days. The solution is filtered and poured onto 14 g of 50% sodium hydroxide solution and ice. The product is extracted into ether. Drying and concentration gives a residue which when triturated with hexane gives material, mp 143°-149° C., suitable for further use.

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