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Synthesis of 14 C‐labelled metoprolol
Author(s) -
Chaudhuri Naba K.,
Ball Thomas J.
Publication year - 1981
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580180904
Subject(s) - chemistry , isopropylamine , metoprolol , methanol , medicinal chemistry , ether , bromide , alcohol , chemical synthesis , stereochemistry , organic chemistry , medicine , biochemistry , cardiology , in vitro
The synthesis of 14 C‐labelled metoprolol, a new antihypertensive drug is described. Starting from p ‐bromoanisole and 14 CO 2 , 14 C‐labelled p ‐methoxyphenylethyl alcohol was prepared by the following sequence of reactions: MeO‐C 6 H 4 ‐Br→ MeO‐C 6 H 4 ‐ 14 COOH→ MeO‐C 6 H 4 ‐ 14 CH 2 OH→ MeO‐C 6 H 4 ‐ 14 CH 2 Cl→ MeO‐C 6 H 4 ‐ 14 CH 2 ‐CN→ MeO‐C 6 H 4 ‐ 14 CH 2 ‐COOH → MeO‐C 6 H 4 ‐ 14 CH 2 ‐CH 2 OH. Heating with 47% HBr gave [ 14 C]‐ p ‐hydroxyphenylethyl bromide which on treatment with methanol under alkaline condition was converted into [ 14 C]‐ p ‐hydroxyphenylethyl methyl ether. Reaction with epichlorhydrin followed by isopropylamine gave [ 14 C]‐metoprolol.