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Synthesis of 1‐chloro‐1‐[ 15 N]nitrosocyclohexane, an electrophilic aminating reagent
Author(s) -
Lodwig Siegfried N.,
Silks Louis A.,
Unkefer Clifford J.
Publication year - 1996
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/(sici)1099-1344(199602)38:2<161::aid-jlcr830>3.0.co;2-l
Subject(s) - chemistry , cyclohexanone , reagent , hydroxylamine , sodium bisulfite , oxime , cyclohexanone oxime , organic chemistry , chlorine , sulfur , yield (engineering) , materials science , metallurgy , catalysis
We have prepared 1‐chloro‐1‐[ 15 N]nitrosocyclohexane, an electrophillic aminating reagent useful for the stereoselective synthesis of α‐[ 15 N]amino acids. Treatment of potassium [ 15 N]nitrate with Pb 0 gave potassium [ 15 N]nitrite, which was converted into the intermediate hydroxylamine disulfonate by treatment with sodium bisulfite and sulfur dioxide. Addition of an excess of cyclohexanone followed by heating gave a mixture of the cyclohexanone [ 15 N]oxime and unreacted cyclohexanone which was removed in vacuo . The resulting [ 15 N]oxime was then converted to 1‐chloro‐1‐[ 15 N]nitrosocyclohexane in essentially quantitative yield by treatment with chlorine gas.