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Synthesis of 1-ethyl-1-(2-hydroxyethyl)aziridinium-1,2-14C2 chloride (1) ([14C]AF64A)

✍ Scribed by Jehangir S. Mistry; Donald J. Abraham; Israel Hanin

Publisher
John Wiley and Sons
Year
1989
Tongue
French
Weight
418 KB
Volume
27
Category
Article
ISSN
0022-2135

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✦ Synopsis

the labelled analogue of a selective presynaptic cholinotoxin, was prepared from labelled ethylene oxide. The synthetic intermediate, 1,2-14C,-2[ethy1[2-[(tetrahydro-2~-pyran-2-yl)oxy]ethyl]amino]ethanol, obtained in good yield by the reaction of 2-[(tetrahydro-2~-pyrann-2-y1)oxy]diethylamine with [W] ethylene oxide, was converted to the corresponding ethyl chloride derivative using CH,SO,Cl/n-BuLi. Subsequent removal of the THP group under mild acidic condition gave the mono-armed mustard as a stable hydrochloride salt in an overall chemical yield of 46% and radiochemical yield of 27%. Conversion of the mustard compound to the corresponding aziridinium species was followed by 'H NMR.

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