The Synthesis of 1-Keto-3-Carbomethoxy-1,2,3,4-Tetrahydroisequinoline

Citation

McGriff, Richard Bernard (1959) The Synthesis of 1-Keto-3-Carbomethoxy-1,2,3,4-Tetrahydroisequinoline. Master's thesis, California Institute of Technology. doi:10.7907/B06Z-W247. https://resolver.caltech.edu/CaltechTHESIS:05102010-153156629

Abstract

The preparation of 1-keto-3-carbomethoxy-1,2,3,4-tetrahydroisequinoline byt wo routes is described. The first involves hydrolysis of the adduct of a-bromo-o-tolunitrile and acetamidomalinicester to 1-keto-3-carboxy-1,2,3,4-tetrahydroisequinoline. Esterification of this acid yields the desired ester. The second route involves the condensation of phenylalanine with formaldehyde to form 3-carboxy-1,2,3,4-tetrahydroisequinoline. The benzoyle derivative of this compounds is smoothly oxidized by cold permanganate to N-benzoyl (o-carboxyphenyl) alanine, wich is convert by acid hydrolysis to 1-keto-3-carboxy-1,2,3,4-tetrahydroisequinoline and benzoic acid. Preliminary experiments show that 1-keto-3-carboxy-1,2,3,4-tetrahydroisequinoline is hydrolyzed by a-chymotrypsin, and indicate that both forms are hydrolyzed,albeit at differing rates.

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