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An improved synthesis of 5,5‐dideuterocyclophosphamide
Author(s) -
Jarman M.,
Taylor G. N.
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.2580180403
Subject(s) - chemistry , yield (engineering) , catalysis , base (topology) , deuterium , weak base , catalytic hydrogenation , organic chemistry , medicinal chemistry , nuclear chemistry , mathematical analysis , materials science , physics , mathematics , quantum mechanics , metallurgy
A high yielding synthesis of 5,5‐dideuterocyclophosphamide is described which involves the base catalysed deuterium exchange of 3‐hydroxypropionitrile and subsequent medium pressure catalytic hydrogenation to yield 1‐amino‐2,2‐dideuteropropan‐3‐ol. This compound is condensed with N,N‐bis(2‐chloroethyl)‐phosphoramidic dichloride to yield pure 5,5‐dideuterocyclophosphamide which is readily isolated as a crystalline monohydrate.