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

Author: McGriff, Richard Bernard

Year: 1959

Degree: Master's thesis

Advisor: Niemann, Carl G.

Committee Member: Unknown, Unknown

Option: Chemistry

DOI: 10.7907/B06Z-W247

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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