Synthesis of deuterium labelled acids

• Published in: Journal of labelled compounds & radiopharmaceuticals Vol. 42; no. 9; pp. 835 - 842
• Main Authors: Kadam, A. J., Desai, U. V., Mane, R. B.
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 01.09.1999; Wiley
• Subjects: Aliphatic compounds; Biochemical Research Methods; Biochemistry & Molecular Biology; Chemistry; Chemistry, Analytical; Chemistry, Medicinal; Exact sciences and technology; Knoevenagel condensation; Life Sciences & Biomedicine; Meldrum's acid; Organic chemistry; Pharmacology & Pharmacy; Physical Sciences; Preparations and properties; Science & Technology; sodium borodeuteride reduction; α-dideuterated; β-monodeuterated and α; β-trideuterated acids; β‐monodeuterated and α,α,β‐trideuterated acids; beta-monodeuterated and alpha,alpha,beta-trideuterated acids; alpha-dideuterated; Knoevenagel condensation; sodium borodeuteride reduction; Meldrum's acid; Deuterium; Furfural; Aliphatic compound; Benzaldehyde; Hydrogen Isotopes; Sodium Tetrahydroborates; Aldehyde; Oxygen heterocycle; Ketone; Carboxylic acid; Benzenic compound; Chemical synthesis; Labelled compound; Acetone
• ISSN: 0362-4803; 1099-1344
• DOI: 10.1002/(SICI)1099-1344(199909)42:9<835::AID-JLCR244>3.0.CO;2-R

Knoevenagel condensation of Meldrum's acid (1) with benzaldehyde, anisaldehyde, furfural, cinnamaldehyde and acetone gave the corresponding alkylidene derivatives (3) which were reduced with sodium borohydride to yield alkyl Meldrum's acids (4). Reaction of (4) with pyridine‐D2O at high temperature furnished α‐dideuterated acids (6). The reduction of alkylidene derivatives (3) with sodium borodeuteride yielded β‐deuterated alkyl Meldrum's acids (7) which on hydrolysis and decarboxylation yielded β‐deuterated acids (9). α,α,β‐Trideuterated acids (11) were prepared by hydrolysis and decarboxylation of (7) with pyridine‐D2O. Copyright © 1999 John Wiley & Sons, Ltd.