Development and Scale-Up of the Electrochemical Dehalogenation for the Synthesis of a Key Intermediate for NS5A Inhibitors

被引：75

作者：

Guetz, Christoph ^{[1
]}

Baenziger, Markus ^{[2
]}

Bucher, Christoph ^{[2
]}

Galvao, Tomas R. ^{[2
]}

Waldvogel, Siegfried R. ^{[1
]}

机构：

[1] Johannes Gutenberg Univ Mainz, Inst Organ Chem, D-55128 Mainz, Germany

[2] Novartis Pharma AG, CH-4056 Basel, Switzerland

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2015年 / 19卷 / 10期

关键词：

REDUCTION; DIMETHYLFORMAMIDE; SALEN;

D O I：

10.1021/acs.oprd.5b00272

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The electrochemical 2-fold dehalogenation of a spirocyclopropane-proline derivative at leaded bronze was scaled-up in a divided batch-type electrolysis cell in good yield and excellent selectivity. The upscaling via a flow electrolysis cell was also successful. Conditions were elaborated employing a single cell passage for complete conversion. The keys here are the direct cooling of the cathode and ensuring a good laminar flow.

引用

页码：1428 / 1433

页数：6

共 41 条

[1] Green Chemistry: Principles and Practice [J].

Anastas, Paul ;

Eghbali, Nicolas .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) :301-312

[2]

[Anonymous], 2014, Angew. Chem

[3]

Baenziger M, 2015, CHIM OGGI, V33, P50

[4]

Beck F., 1974, ELEKTROORGANISCHE CH

[5]

Cao H., 2012, World Patent, Patent No. [WO 2012/059281 A2, 2012059281]

[6] Stereoselective cathodic synthesis of 8-substituted (1R,3R,4S)-menthylamines [J].

Edinger, Carolin ;

Kulisch, Joern ;

Waldvogel, Siegfried R. .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 :294-301

[7] Electrochemical Deoxygenation of Aromatic Amides and Sulfoxides [J].

Edinger, Carolin ;

Waldvogel, Siegfried R. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (24) :5144-5148

[8] Stabilizing Lead Cathodes with Diammonium Salt Additives in the Deoxygenation of Aromatic Amides [J].

Edinger, Carolin ;

Grimaudo, Valentine ;

Broekmann, Peter ;

Waldvogel, Siegfried R. .

CHEMELECTROCHEM, 2014, 1 (06) :1018-1022

[9]

Eisler B., 2014, ANGEW CHEM, V126, P5311

[10] Metal- and Reagent-Free Highly Selective Anodic Cross-Coupling Reaction of Phenols [J].

Elsler, Bernd ;

Schollmeyer, Dieter ;

Dyballa, Katrin Marie ;

Franke, Robert ;

Waldvogel, Siegfried R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (20) :5210-5213

← 1 2 3 4 5 →