Efficient one-pot synthesis of the GABAB positive allosteric modulator (R,S)-5,7-di-tert-butyl-3-hydroxy-3-trifluoromethyl-3H-benzofuran-2-one

被引：6
|
作者：
Alker, Andre M. [1 ]
Grillet, Francois [1 ]
Malherbe, Pari [1 ]
Norcross, Roger D. [1 ]
Thomas, Andrew W. [1 ]
Masciadri, Raffaello [1 ]
机构：
[1] Hoffmann La Roche Ag, CH-4002 Basel, Switzerland
来源：
SYNTHETIC COMMUNICATIONS | 2008年 / 38卷 / 20期
关键词：
(R, S)-5,7-di-tert-butyl-3-hydroxy-3-trifluoromethyl-3H-benzofuran-2-one; GABA(B) positive allosteric modulator; gallium(III) chloride; one-pot synthesis;
D O I：
10.1080/00397910801979403
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The GABA(B) positive allosteric modulator (R,S)-5,7-di-tert-butyl-3-hydroxy-3-trifluoromethyl-3H-benzofuran-2-one (1) was synthesized in one pot from the anhydrous lithium salt of 2,4-di-tert-butylphenol and methyl trifluoropyruvate mediated by a stoichiometric amount of anhydrous gallium(III) chloride in 64% overall yield. The enantiomers of 1 were separated by chiral-phase HPLC (Chiralpak AD (R)), and the absolute configuration was determined by X-ray crystallography.
引用
收藏
页码：3398 / 3405
页数：8
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