A simple method for α‐position deuterated carbonyl compounds with pyrrolidine as catalyst†. (3rd July 2014)

• Record Type: Journal Article
• Authors: Zhan, Miao; Zhang, Tao; Huang, Haoxi; Xie, Yongmei; Chen, Yuanwei
• Is Part Of: Journal of labelled compounds & radiopharmaceuticals. Volume 57:Number 8(2014)
• Page Start: 533
• Page End: 539
• Publication Date: 2014-07-03
• Subjects: Tracers (Chemistry) -- Periodicals; Radiopharmaceuticals -- Periodicals; 615.8424
• DOI: 10.1002/jlcr.3210
• Languages: English
• ISSNs: 0362-4803

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>A simple, cost‐effective method for deuteration of carbonyl compounds employing pyrrolidine as catalyst and D₂O 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.</p> </abstract>