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%). However, the reduction of oximino esters with LiAlH<sub>4</sub> and BH<sub>3</sub>. Tetrahydrofuran 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>