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

Kucuk H. B., Yasa H., Yildiz T., Yusufoglu A. S.

SYNTHETIC COMMUNICATIONS, vol.47, no.22, pp.2070-2077, 2017 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 47 Issue: 22
  • Publication Date: 2017
  • Doi Number: 10.1080/00397911.2017.1364768
  • Journal Name: SYNTHETIC COMMUNICATIONS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2070-2077
  • Istanbul University Affiliated: Yes

Abstract

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.