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

The preparation of novel 3-, 4-, 6-, and 13-amino-tetradecanoic acid methyl esters (2a-d) obtained by the reduction of 3-, 4-, 6-, and 13-oximino-tetradecanoic acid methyl esters (1a-d), was investigated. Oximino esters were reduced to afford the corresponding amino esters using NaBH4-ZrCl4 reducing system with good yields (58-82%). However, the reduction of oximino esters with LiAlH4 and BH3. Tetrahydrofuran gave the corresponding novel 3-, 4-, 6-, and 13-oximino alcohols (3a-d), and 3-, 4-, 6-, and 13-amino alcohols (4a-d) respectively with good chemical yields.