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

• Published in: Steroids Vol. 60; no. 6; pp. 453 - 457
• Main Authors: Dayal, B., Rao, Keshava, Salen, G.
• Format: Journal Article
• Language: English
• Published: WOBURN Elsevier Inc 01.06.1995; Butterworth-Heinemann; Elsevier Science
• Subjects: Acetylation; Alicyclic compounds, terpenoids, prostaglandins, steroids; Benzenesulfonates - pharmacology; bile acids; Bile Acids and Salts - chemistry; Biochemistry & Molecular Biology; Chemistry; Cholic Acid; Cholic Acids - chemistry; deacetylation; deformylation; Endocrinology & Metabolism; Esterification; Exact sciences and technology; Indicators and Reagents; Life Sciences & Biomedicine; Lithocholic Acid - analogs & derivatives; Lithocholic Acid - chemistry; Mesylates - pharmacology; methanesulfonic acid/methanol; microwave; Microwaves; Molecular Structure; Organic chemistry; para-toluene sulfonic acid/methanol; Preparations and properties; Science & Technology; Steroids; methanesulfonic acid/methanol; esterification; bile acids; deacetylation; para-toluene sulfonic acid/methanol; deformylation; microwave; DEFORMYLATION; DEACETYLATION; OVEN; MICROWAVE; METHANESULFONIC ACID METHANOL; ESTERIFICATION; PARA-TOLUENE SULFONIC ACID METHANOL; BILE ACIDS; METHYL-ESTERS; Sonochemical reaction; Steroid; Catalytic reaction; Mild operating conditions; Saturated compound; Ketol; Esterification; Organic solvent; Microwave oven; Carboxylic acid; Deacetylation; Bile acid; Formylation; Secondary alcohol; Methanol
• ISSN: 0039-128X; 1878-5867
• DOI: 10.1016/0039-128X(95)00004-A

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-5β-cholestanoic acid, (23R)-3α,7α,23-trihydroxy-5β-cholan-24-oic acid, ursocholic acid and 7-ketolithocholic acid were isolated in 86–94% yield.