Aminolysis of Epoxides in a Microreactor System: A Continuous Flow Approach to β-Amino Alcohols

被引：121

作者：

Bedore, Matthew W. ^{[2
]}

Zaborenko, Nikolay ^{[1
]}

Jensen, Klavs F. ^{[1
]}

Jamison, Timothy F. ^{[2
]}

机构：

[1] MIT, Dept Chem Engn, Cambridge, MA 02139 USA

[2] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2010年 / 14卷 / 02期

关键词：

CHEMOSELECTIVE ADDITION; REUSABLE CATALYST; HIGHLY EFFICIENT; SCALE-UP; MICROWAVE; ROUTE; MILD;

D O I：

10.1021/op9003136

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The use of a continuous flow microreactor for beta-amino alcohol formation by epoxide aminolysis is evaluated. Comparison to microwave batch reactions reveals that conditions obtainable in the microreactor can match or improve yields in many eases. By increasing the pressure of the system, maximum temperatures can also exceed those accessible using a microwave unit. The use of a microreactor for epoxide aminolysis reactions in the synthesis of two pharmaceutical relevant compounds is described.

引用

收藏

页码：432 / 440

页数：9

相关论文

共 43 条

[31] An efficient and economical synthesis of 5,6-diethyl-2,3-dihydro-1H-inden-2-amine hydrochloride [J].

Prashad, M ;

Hu, B ;

Har, D ;

Repic, J ;

Blacklock, TJ .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2006, 10 (01) :135-141

[32] Highly efficient and versatile chemoselective addition of amines to epoxides in water catalyzed by erbium(III) triflate [J].

Procopio, Antonio ;

Gaspari, Marco ;

Nardi, Monica ;

Oliverio, Manuela ;

Rosati, Ornelio .

TETRAHEDRON LETTERS, 2008, 49 (14) :2289-2293

[33] Continuous-Flow Microreactor Chemistry under High-Temperature/Pressure Conditions [J].

Razzaq, Tahseen ;

Glasnov, Toma N. ;

Kappe, C. Oliver .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (09) :1321-1325

[34]

ROA AVR, 1997, Patent No. 177748

[35] Microreactor technology and continuous processes in the fine chemical and pharmaceutical industry: Is the revolution underway? [J].

Roberge, Dominique M. ;

Zimmermann, Bertin ;

Rainone, Fabio ;

Gottsponer, Michael ;

Eyholzer, Markus ;

Kockmann, Norbert .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2008, 12 (05) :905-910

[36] Microwave-assisted ring opening of epoxides: A general route to the synthesis of 1-aminopropan-2-ols with anti malaria parasite activities [J].

Robin, Aelig ;

Brown, Fraser ;

Bahamontes-Rosa, Noemi ;

Wu, Binghua ;

Beitz, Eric ;

Kun, Jurgen F. J. ;

Flitsch, Sabine L. .

JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (17) :4243-4249

[37] Pharmacological characterization of indacaterol, a novel once daily inhaled β2 adrenoceptor agonist, on small airways in human and rat precision-cut lung slices [J].

Sturton, Richard G. ;

Trifilieff, Alexandre ;

Nicholson, Andrew G. ;

Barnes, Peter J. .

JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2008, 324 (01) :270-275

[38]

TACHIBANA S, 2007, Patent No. 200765354

[39] Amberlist-15 as heterogeneous reusable catalyst for regioselective ring opening of epoxides with amines under mild conditions [J].

Vijender, Medamoni ;

Kishore, P. ;

Narender, P. ;

Satyanarayana, B. .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 266 (1-2) :290-293

[40] BENEFICIAL-EFFECTS OF METOPROLOL IN IDIOPATHIC DILATED CARDIOMYOPATHY [J].

WAAGSTEIN, F ;

BRISTOW, MR ;

SWEDBERG, K ;

CAMERINI, F ;

FOWLER, MB ;

SILVER, MA ;

GILBERT, EM ;

JOHNSON, MR ;

GOSS, FG ;

HJALMARSON, A .

LANCET, 1993, 342 (8885) :1441-1446

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