Synthesis of esters of tetradecanoic acid deuterated at the penultimate carbon: Some general procedures for the synthesis of selectively deuterated fatty acids

✍ Scribed by P.W. Westerman; N. Ghrayeb

• Publisher: Elsevier Science
• Year: 1982
• Tongue: English
• Weight: 368 KB
• Volume: 30
• Category: Article
• ISSN: 0009-3084
• DOI: 10.1016/0009-3084(82)90031-7

✦ Synopsis

Methyl tetradecanoate, deuterated in the penultimate position has been prepared by three synthetic routes. One method in which an oxoester is an intermediate, utilizes the selective reducing properties of sodium borodeuteride and sodium cyanoborodeuteride towards oxo, tosyloxy and ester groups to introduce the deuterium label at only the oxo carbon of the oxoester. The second procedure, introduces a single deuterium at the oxo carbon of an oxoester, in a selective deoxygenation step which reduces an intermediate tosylhydrazone with sodium cyanoborodeuteride in acidic dimethylformamide-sulfolane. The third pathway, couples lithium dimethylcuprate (I) to the tosylate derivative of a to-deuterio-to-hydroxy methylester, prepared from the half-ester of a dicarboxylic acid. Utilizing suitable modifications, these three methods should be generally applicable in the synthesis of any saturated straight-chain alkanoate, selectively deuterated in the penultimate (to -1) carbon, or at any other carbon in the hydrocarbon chain.