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A simple method for α ‐position deuterated carbonyl compounds with pyrrolidine as catalyst
Author(s) -
Zhan Miao,
Zhang Tao,
Huang Haoxi,
Xie Yongmei,
Chen Yuanwei
Publication year - 2014
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.3210
Subject(s) - pyrrolidine , chemistry , catalysis , cyclohexene , deuterium , hydrolysis , hydrogen–deuterium exchange , organic chemistry , medicinal chemistry , hydrogen , physics , quantum mechanics
A simple, cost‐effective method for deuteration of carbonyl compounds employing pyrrolidine as catalyst and D 2 O as deuterium source was described. High degree of deuterium incorporation (up to 99%) and extensive functional group tolerance were achieved. It is the first time that secondary amines are used as catalysts for H/D exchange of carbonyl compounds, which also allow the deuteration of complex pharmaceutically interesting substrates. A possible catalytic mechanism, based on the hydrolysis of 1‐pyrrolidino‐1‐cyclohexene, for this pyrrolidine‐catalyzed H/D exchange reaction has been proposed.