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

被引：23

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

页码：533 / 539

页数：7

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