Microwave-induced organic reactions of bile acids: esterification, deformylation and deacetylation using mild reagents

Steroids. 1995 Jun;60(6):453-7. doi: 10.1016/0039-128x(95)00004-a.

Abstract

An efficient and convenient procedure for the esterification, deformylation, and deacetylation of bile acids is described. This is achieved by the addition of a catalytic amount of methanesulfonic acid or para-toluene sulfonic acid to a solution of bile acid in methanol in the domestic microwave oven. All these reactions were completed in the microwave oven within 1-3 min at 60% power (390 W) and the desired bile acids, namely trihydroxy-5 beta-cholestanoic acid, (23R)-3 alpha,7 alpha,23-trihydroxy-5 beta-cholan-24-oic acid, ursocholic acid and 7-ketolithocholic acid were isolated in 86-94% yield.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Acetylation
  • Benzenesulfonates / pharmacology
  • Bile Acids and Salts / chemistry*
  • Cholic Acid
  • Cholic Acids / chemistry
  • Esterification
  • Indicators and Reagents
  • Lithocholic Acid / analogs & derivatives
  • Lithocholic Acid / chemistry
  • Mesylates / pharmacology
  • Microwaves*
  • Molecular Structure

Substances

  • Benzenesulfonates
  • Bile Acids and Salts
  • Cholic Acids
  • Indicators and Reagents
  • Mesylates
  • methanesulfonic acid
  • 7-ketolithocholic acid
  • Lithocholic Acid
  • Cholic Acid
  • ursocholic acid
  • cholanic acid
  • 4-toluenesulfonic acid