Microwave-assisted cobinamide synthesis

J Org Chem. 2014 Aug 15;79(16):7752-7. doi: 10.1021/jo501364b. Epub 2014 Jul 31.

Abstract

We present a new method for the preparation of cobinamide (CN)2Cbi, a vitamin B12 precursor, that should allow its broader utility. Treatment of vitamin B12 with only NaCN and heating in a microwave reactor affords (CN)2Cbi as the sole product. The purification procedure was greatly simplified, allowing for easy isolation of the product in 94% yield. The use of microwave heating proved beneficial also for (CN)2Cbi(c-lactone) synthesis. Treatment of (CN)2Cbi with triethanolamine led to (CN)2Cbi(c-lactam).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cobamides / chemical synthesis*
  • Cobamides / chemistry
  • Ethanolamines / chemistry*
  • Lactams, Macrocyclic / chemical synthesis*
  • Lactams, Macrocyclic / chemistry
  • Microwaves
  • Vitamin B 12 / chemistry*

Substances

  • Cobamides
  • Ethanolamines
  • Lactams, Macrocyclic
  • cobinamide
  • triethanolamine
  • Vitamin B 12