A simple method for α-position deuterated carbonyl compounds with pyrrolidine as catalyst

被引：25
|
作者：
Zhan, Miao [1 ]
Zhang, Tao [1 ]
Huang, Haoxi [2 ]
Xie, Yongmei [1 ]
Chen, Yuanwei [1 ,3 ]
机构：
[1] Sichuan Univ, West China Med Sch, State Key Lab Biotherapy, West China Hosp, Chengdu 610041, Peoples R China
[2] Chengdu ChemPartner Co Ltd, Chengdu 610041, Peoples R China
[3] Chengdu HC Pharmaceut Co Ltd, Chengdu 610041, Peoples R China
来源：
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS | 2014年 / 57卷 / 08期
关键词：
isotope exchange; deuterium; chemoselectivity; ketones; deuterium oxide; pyrrolidine; H/D-EXCHANGE-REACTIONS; DEUTERIUM; NMR; ELIMINATION; MECHANISM; LIGANDS; TRITIUM; STATE; PD/C; C-13;
D O I：
10.1002/jlcr.3210
中图分类号：
Q5 [生物化学];
学科分类号：
071010 ; 081704 ;
摘要：
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.
引用
收藏
页码：533 / 539
页数：7
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