A detailed studies on the reduction of aliphatic 3-, 4-, 6- and 13-oximino esters: Synthesis of novel isomeric amino esters, oximino alcohols, and amino alcohols

<p>The preparation of novel 3-, 4-, 6-, and 13-amino-tetradecanoic acid methyl esters (<b>2a-d</b>) obtained by the reduction of 3-, 4-, 6-, and 13-oximino-tetradecanoic acid methyl esters (<b>1a-d</b>), was investigated. Oximino esters were reduced to afford the corresponding amino esters using NaBH<sub>4</sub>-ZrCl<sub>4</sub> reducing system with good yields (58-82%). On the other hand, the reduction of oximino esters with LiAlH<sub>4</sub> and BH<sub>3. T</sub>HF gave the corresponding novel 3-, 4-, 6-, and 13-oximino alcohols (<b>3a-d</b>), and 3-, 4-, 6-, and 13-amino alcohols (<b>4a-d</b>) respectively with good chemical yields.</p>