8-Aminooctanoic acid

Aminopentanoic acid (7.5) is known as 8-aminovaleric acid and given the abbreviation DAVA. Both 6-aminohexanoic acid (7.4), also known as aminocaproic acid, and 7-aminoheptanoic acid (7.5) are well known. 8-Aminooctanoic acid (7.5),... 

Aldehydes and ketones serve as useful precursors to amino acids when they are converted to a Schiff base (from aldehydes) or an imine (from ketones). Reduction of the imino C=N moiety, usually in situ, generates the amine. When 1.83 (m = 1, 2) was treated with ammonia, for example, the resulting iminium salt (1,84) was hydrogenated to give either 8-aminooctanoic acid (7.[Pg.18]

Another important method for the preparation of amino acids involves direct cleavage of a cyclic ketone. In section 2.1.A, a lactam product (a cyclic amide) was produced from the ketone and then cleaved by hydrolysis, but in this section the ketone moiety is cleaved directly. A cyclic ketone such as cyclopentanone can be oxidatively cleaved with sulfuric acid. When this cleavage was followed by treatment with nitrosyl sulfate, an oximino acid 2.11) was formed. Catalytic hydrogenation of the oximino group gave 4-aminobutanoic acid (2.72). Similar treatment of cycloheptanone gave 6-aminohexanoic acid (2.75) and cyclononanone led to 8-aminooctanoic acid. ... 

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