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Synthesis of carbon‐14 labelled ropivacaine, a local anaesthetic agent
Author(s) -
Sahlberg Christer
Publication year - 1987
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.2580240508
Subject(s) - chemistry , ropivacaine , hydrochloride , carboxamide , local anaesthetic , piperidine , methyl iodide , iodide , medicinal chemistry , stereochemistry , nuclear chemistry , pharmacology , organic chemistry , anesthesia , medicine
Ropivacaine hydrochloride monohydrate (LEA 103) is a new local anaesthetic agent which currently is under preclinical and clinical investigation. The preparation of (S)‐N‐(2,6‐[2‐methyl‐ 14 C]dimethylphenyl)‐1‐propylpiperidine‐2‐carboxamide hydrochloride monohydrate ( 6 , [ 14 C]‐LEA 103) with a specific activity of 12.44 mCi/mmol is described. The key step in the synthesis is a Pd(II)‐mediated reaction of (S)‐1‐benzyloxycarbonyl‐N‐(2‐methylphenyl)‐piperidine‐2‐carboxamide ( 3 ) with [ 14 C]methyl iodide. Also described is the preparation of compound 3 from (S)‐2‐piperidinecarboxylic acid.