A Low-Waste Process To Sertraline By Diastereomeric Crystal Resolution and Waste Isomer Racemisation

被引：15

作者：

Blacker, A. John ^{[1
]}

Brown, Stuart ^{[1
]}

Clique, Blandine ^{[1
]}

Gourlay, Brian ^{[1
]}

Headley, Catherine E. ^{[1
]}

Ingham, Stephen ^{[1
]}

Ritson, Dougal ^{[1
]}

Screen, Thomas ^{[1
]}

Stirling, Matthew J. ^{[1
]}

Taylor, David ^{[1
]}

Thompson, Gary ^{[1
]}

机构：

[1] Piramal Healthcare Res & Dev, Huddersfield, W Yorkshire, England

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2009年 / 13卷 / 06期

关键词：

DYNAMIC KINETIC RESOLUTION; INDUCED ASYMMETRIC TRANSFORMATION; CHIRAL AMINES; ENZYMATIC RESOLUTION; SECONDARY-AMINES; LIPASE; ACID; NANOFILTRATION; CATALYST; SOLVENT;

D O I：

10.1021/op900112f

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A semi-continuous method for recovering waste sertraline isomers from a diastereomeric crystallisation process is described in which the mother liquors from a highly selective mandelic acid resolution for the (1S,4S) isomer are treated sequentially with SCRAM, an iridium-based chiral amine racemisation catalyst, and then catalytic potassium tertiary butoxide to epimerise the methine chiral centre. The green, low-waste process also deals with recovery and recycle of the precious-metal catalyst, providing both good economics and high-quality product.

引用

页码：1370 / 1378

页数：9

共 37 条

[1] Developing processes for crystallization-induced asymmetric transformation [J].

Anderson, NG .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2005, 9 (06) :800-813

[2] Catalytic racemisation of chiral amines and application in dynamic kinetic resolution [J].

Blacker, A. John ;

Stirling, Matthew J. ;

Page, Michael I. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (03) :642-648

[3]

BRAISH TF, 1992, Patent No. 5082970

[4] Crystallization-induced diastereomer transformations [J].

Brands, Karel M. J. ;

Davies, Antony J. .

CHEMICAL REVIEWS, 2006, 106 (07) :2711-2733

[5] Enzymatic resolution of a secondary amine using novel acylating reagents [J].

Breen, GF .

TETRAHEDRON-ASYMMETRY, 2004, 15 (09) :1427-1430

[6] NEW ASYMMETRIC TRANSFORMATION OF ALPHA-AMINO-ACID ESTERS WITH (+)-TARTARIC ACID [J].

CLARK, JC ;

PHILLIPPS, GH ;

STEER, MR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (05) :475-481

[7] Modelling a river catchment using an electrical circuit analogue [J].

Collier, CG .

HYDROLOGY AND EARTH SYSTEM SCIENCES, 1998, 2 (01) :9-18

[8]

DUCKETT S, 725450 CCDC U YORK, P47209

[9] Controlled racemization of optically active organic compounds: Prospects for asymmetric transformation [J].

Ebbers, EJ ;

Ariaans, GJA ;

Houbiers, JPM ;

Bruggink, A ;

Zwanenburg, B .

TETRAHEDRON, 1997, 53 (28) :9417-9476

[10] An improved protocol for the synthesis and nanofiltration of Kim and Park's aminocyclopentadienyl ruthenium chloride racemisation catalyst [J].

Gibbins, EJ ;

Irwin, JL ;

Livingston, AG ;

Muir, JC ;

Patterson, DA ;

Roengpithya, C ;

Taylor, PC .

SYNLETT, 2005, (19) :2993-2995

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