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

页码：3398 / 3405

页数：8

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