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Synthesis of cyclopropyl cyanide‐2,2‐d 2
Author(s) -
Edwardsiii William B.,
Glenn David F.
Publication year - 1976
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.2580120117
Subject(s) - chemistry , cyanide , iodide , triphenylphosphine , sodium cyanide , methyl iodide , sodium iodide , sodium hydride , alcohol , yield (engineering) , deuterium , medicinal chemistry , sodium , lithium (medication) , carbon tetrachloride , organic chemistry , catalysis , medicine , materials science , physics , quantum mechanics , metallurgy , endocrinology
A convenient method for the synthesis of cyclopropyl cyanide‐2,2‐ d 2 has been elaborated. Reduction of methyl 3‐cyanopropionate with lithium borodeuteride followed by reaction of the resulting alcohol with triphenylphosphine and carbon tetrachloride gave 4‐chlorobutyronitrile‐4,4‐ d 2 . Conversion of the chloride to the iodide with sodium iodide followed by cyclization with sodium hydride afforded cyclopropyl cyanide‐2,2‐ d 2 in 30% overall yield with deuterium incorporation of > 95%.