Table of Contents

May 2007
Volume 11, Issue 3
Pages 297-650
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Editorial

Could This Happen in Your Company?

Trevor Laird
pp 297–298
Publication Date (Web): May 03, 2007 (Editorial)
DOI: 10.1021/op700082b
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Highlights from the Literature

Some Items of Interest to Process R&D Chemists and Engineers

Mark McLaughlinSilvina García RubioUlf TilstamOctavio Augusto Ceva AntunesGanapati D. YadavAndrei ZlotaTrevor Laird
pp 299–310
Publication Date (Web): May 04, 2007 (Highlights from the Literature)
DOI: 10.1021/op7000832
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Regulatory Highlights

Regulatory Highlights for 2006 to March 2007

Derek Robinson
pp 311–317
Publication Date (Web): March 30, 2007 (Editorial)
DOI: 10.1021/op700057c
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Highlights from the Patents

A Review of U.S. Patents in the Field of Organic Process Development Published during October to December 2006

Keith Turner
pp 318–327
Publication Date (Web): April 18, 2007 (Highlights From Patents)
DOI: 10.1021/op700071a

Full Papers

From High-Throughput Catalyst Screening to Reaction Optimization:  Detailed Investigation of Regioselective Suzuki Coupling of 1,6-Naphthyridone Dichloride

Chaoxian Cai, John Y. L. Chung, J. Christopher McWilliams, Yongkui Sun, C. Scott Shultz, and Michael Palucki
pp 328–335
Publication Date (Web): April 21, 2007 (Article)
DOI: 10.1021/op060215e

An Improved Manufacturing Process for the Antimalaria Drug Coartem. Part I

Matthias Boehm, Peter C. Fuenfschilling, Matthias Krieger, Ernst Kuesters, and Fritz Struber
pp 336–340
Publication Date (Web): April 28, 2007 (Article)
DOI: 10.1021/op0602425

An Improved Manufacturing Process for the Antimalaria Drug Coartem. Part II

Ulrich Beutler, Peter C. Fuenfschilling, and Andreas Steinkemper
pp 341–345
Publication Date (Web): April 28, 2007 (Article)
DOI: 10.1021/op060244p

Process Development and Scale-up for (±)-Reboxetine Mesylate

Kevin E. Henegar, Cynthia T. Ball, Carolyn M. Horvath, Keith D. Maisto, and Sarah E. Mancini
pp 346–353
Publication Date (Web): March 23, 2007 (Article)
DOI: 10.1021/op7000063

Process Development for (S,S)-Reboxetine Succinate via a Sharpless Asymmetric Epoxidation

Kevin E. Henegar and Mateusz Cebula
pp 354–358
Publication Date (Web): March 23, 2007 (Article)
DOI: 10.1021/op700007g

Suppression of a Palladium-Mediated Homocoupling in a Suzuki Cross-Coupling Reaction. Development of an Impurity Control Strategy Supporting Synthesis of LY451395

William D. Miller, Andrew H. Fray, John T. Quatroche, and Christa D. Sturgill
pp 359–364
Publication Date (Web): April 18, 2007 (Article)
DOI: 10.1021/op060180i

An Approach to Early-Phase Salt Selection:  Application to NBI-75043

Timothy D. Gross, Kevin Schaab, Michael Ouellette, Scott Zook, Jayachandra P. Reddy, Arthur Shurtleff, Aida I. Sacaan, Tanja Alebic-Kolbah, and Haig Bozigian
pp 365–377
Publication Date (Web): March 27, 2007 (Article)
DOI: 10.1021/op060221a

Development of a Commercial Process to Produce Oxandrolone

John E. Cabaj, David Kairys, and Thomas R. Benson
pp 378–388
Publication Date (Web): April 20, 2007 (Article)
DOI: 10.1021/op060231b

Practical Synthesis and Molecular Structure of a Potent Broad-Spectrum Antibacterial Isothiazoloquinolone

Akihiro Hashimoto, Godwin C. G. Pais, Qiuping Wang, Edlaine Lucien, Christopher D. Incarvito, Milind Deshpande, Barton J. Bradbury, and Jason A. Wiles
pp 389–398
Publication Date (Web): March 16, 2007 (Article)
DOI: 10.1021/op700014t

A Microcapillary Flow Disc Reactor for Organic Synthesis

Christian H. Hornung, Malcolm R. Mackley, Ian R. Baxendale, and Steven V. Ley
pp 399–405
Publication Date (Web): April 24, 2007 (Article)
DOI: 10.1021/op700015f

Highly Functionalised Sulfur-Based Silica Scavengers for the Efficient Removal of Palladium Species from Active Pharmaceutical Ingredients

Nicola Galaffu, Siud Pui Man, Robin D. Wilkes, and John R. H. Wilson
pp 406–413
Publication Date (Web): April 28, 2007 (Article)
DOI: 10.1021/op7000172

Synthesis of Tetracyclic Heterocompounds as Selective Estrogen Receptor Modulators. Part 1. Process Development for Scale-up of 2,5,8-Substituted 5,11-Dihydrochromeno[4,3-c]chromene Derivatives

Xun Li, Michael Reuman, Ronald K. Russell, Richard Adams, Robert Ma, Sandra Beish, Shawn Branum, Scott Youells, Jerry Roberts, Nareshkumar Jain, Ramesh Kanojia, and Zhihua Sui
pp 414–421
Publication Date (Web): March 31, 2007 (Article)
DOI: 10.1021/op700020f

Scale-Up Syntheses of Two Naturally Occurring Procyanidins:  (−)-Epicatechin-(4β,8)-(+)-catechin and (−)-Epicatechin-3-O-galloyl-(4β,8)-(−)-epicatechin-3-O-gallate

Pradeep K. Sharma, Alexander Kolchinski, Hélène A. Shea, Jayesh J. Nair, Yanni Gou, Leo J. Romanczyk, Jr., and Harold H. Schmitz
pp 422–430
Publication Date (Web): April 26, 2007 (Article)
DOI: 10.1021/op700031n

A Convergent Kilogram-Scale Synthesis of the PPARα Agonist LY518674:  Discovery of a Novel Acid-Mediated Triazolone Synthesis

Timothy M. Braden, D. Scott Coffey, Christopher W. Doecke, Michael E. LeTourneau, Michael J. Martinelli, Christopher L. Meyer, Richard D. Miller, Joseph M. Pawlak, Steven W. Pedersen, Christopher R. Schmid, Bruce W. Shaw, Michael A. Staszak, and Jeffrey T. Vicenzi
pp 431–440
Publication Date (Web): April 06, 2007 (Article)
DOI: 10.1021/op700040v

The Preparation of Two, Preclinical Amino-quinazolinediones as Antibacterial Agents

Vladimir Beylin, David C. Boyles, Timothy T. Curran, Dainius Macikenas, Roger V. Parlett, IV, and Derek Vrieze
pp 441–449
Publication Date (Web): May 04, 2007 (Article)
DOI: 10.1021/op7000639

Communications to the Editor

An Efficient Synthesis of Dibenzo[c,f]-2,7-naphthyridine Ring System through Design of Experiments

Ariamala Gopalsamy, Mengxiao Shi, and Ramaswamy Nilakantan
pp 450–454
Publication Date (Web): March 27, 2007 (Communication to Editor)
DOI: 10.1021/op700009t

An Alternative Approach to Achieve Enantiopure (3S)-4-Benzyl-3- (4-fluorophenyl)morpholin-2-one:  A Key Intermediate of Aprepitant, an NK1 Receptor Antagonist

Naveenkumar Kolla, Chandrashekar R. Elati, Muthulingam Arunagiri, Srinivas Gangula, Pravinchandra J. Vankawala, Yerremilli Anjaneyulu, Apurba Bhattacharya, Sundaram Venkatraman, and Vijayavitthal T. Mathad
pp 455–457
Publication Date (Web): May 04, 2007 (Communication to Editor)
DOI: 10.1021/op700030d

Continuous Flow Ligand-Free Heck Reactions Using Monolithic Pd [0] Nanoparticles

Nikzad Nikbin, Mark Ladlow, and Steven V. Ley
pp 458–462
Publication Date (Web): April 07, 2007 (Communication to Editor)
DOI: 10.1021/op7000436

Improved and Practical Synthesis of 6-Methoxy-1,2,3,4- tetrahydroisoquinoline Hydrochloride

H. Marlon Zhong, Frank J. Villani, and Ramzy Marzouq
pp 463–465
Publication Date (Web): April 25, 2007 (Article)
DOI: 10.1021/op7000468

Technical Notes

An Improved Process for the Preparation of 4,4-Dimethyloxazolidine-2-thione

Neera Tewari, Dinesh Nair, Hashim Nizar, Bishwa Prakash Rai, and Mohan Prasad
pp 466–467
Publication Date (Web): April 03, 2007 (Technical Note)
DOI: 10.1021/op6002677

A Facile Process for the Preparation of 2-Bromoethyl Methyl Ether

Varaprasad Dasari, Rao V. Srinivas,Rao V. Srinivas, Sunil R. Rao, Kalyan Chakravarthy Akula, Ravi Dhamjewar, and Yogesh S. Sanghvi
pp 468–469
Publication Date (Web): March 16, 2007 (Technical Note)
DOI: 10.1021/op060229k

A Green Chemistry Comparative Analysis of the Syntheses of (E)-4-Cyclobutyl-2-[2-(3-nitrophenyl)ethenyl] Thiazole, Ro 24-5904

Michael A. Kuzemko, Susan D. Van Arnum, and Henry J. Niemczyk
pp 470–476
Publication Date (Web): April 07, 2007 (Technical Note)
DOI: 10.1021/op700008k

QuadraPure Cartridges for Removal of Trace Metal from Reaction Mixtures in Flow

A. Hinchcliffe, C. Hughes, D. A. Pears, and M. R. Pitts
pp 477–481
Publication Date (Web): April 28, 2007 (Technical Note)
DOI: 10.1021/op7000113

High-Yielding Syntheses of 1-Piperidin-4-yl Butyro- and Valerolactams through a Tandem Reductive Amination−Lactamization (Reductive Lactamization)

Christopher M. Mapes and Neelakandha S. Mani
pp 482–486
Publication Date (Web): April 19, 2007 (Technical Note)
DOI: 10.1021/op700016b

Synthetic Improvements in the Preparation of Clopidogrel

Lixin Wang, Jianfen Shen, Yi Tang, Yi Chen, Wen Wang, Zegui Cai, and Zhenjun Du
pp 487–489
Publication Date (Web): March 31, 2007 (Technical Note)
DOI: 10.1021/op700025d

New Practical Synthesis of the Key Intermediate of Candesartan

Márta Porcs-Makkay, Tibor Mezei, and Gyula Simig
pp 490–493
Publication Date (Web): April 25, 2007 (Technical Note)
DOI: 10.1021/op700041z

SPECIAL FEATURE SECTION: ASYMMETRIC SYNTHESIS ON LARGE SCALE
Editorial

SPECIAL FEATURE SECTION:  ASYMMETRIC SYNTHESIS ON LARGE SCALE

Hans Jürgen FederselKarel M. J. Brands
p 494
Publication Date (Web): May 18, 2007 (Editorial)
DOI: 10.1021/op700081f
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Reviews

Catalytic Asymmetric Carbon−Carbon Bond Formations:  Their Evolution from Biocatalysis to Organocatalysis over the Millennium

Masaya Ikunaka
pp 495–502
Publication Date (Web): December 09, 2006 (Review)
DOI: 10.1021/op050161t

Bioreactor Systems for the Production of Optically Active Amino Acids and Alcohols

Hirokazu Nanba, Yoshihiko Yasohara, Junzo Hasegawa, and Satomi Takahashi
pp 503–508
Publication Date (Web): January 26, 2007 (Review)
DOI: 10.1021/op060129e

Practical Copper-Catalyzed Asymmetric Synthesis of Chiral Chrysanthemic Acid Esters

Makoto Itagaki and Katsuhiro Suenobu
pp 509–518
Publication Date (Web): March 23, 2007 (Review)
DOI: 10.1021/op060238t

Full Papers

Enantioselective Ketone Hydrogenation:  From R&D to Pilot Scale with Industrially Viable Ru/Phosphine−Oxazoline Complexes

Frédéric Naud, Felix Spindler, Carsten J. Rueggeberg, Andreas T. Schmidt, and Hans-Ulrich Blaser
pp 519–523
Publication Date (Web): January 09, 2007 (Article)
DOI: 10.1021/op0601619

Enantioselective Synthesis of a Key Intermediate in a New Process for Orlistat Using Asymmetric Hydrogenation and a Grignard Reagent Promoted Lactone Cyclization

Mark A. Schwindt, Michael P. Fleming, Yeun-Kwei Han, Lewis M. Hodges, David A. Johnston, Roger P. Micheli, Chris R. Roberts, Roger Snyder, Robert J. Topping, Kurt Püntener, and Michelangelo Scalone
pp 524–533
Publication Date (Web): January 09, 2007 (Article)
DOI: 10.1021/op060208q

Development of an Asymmetric Acetate Aldol Reaction with a Trifluoromethyl Ketone

Jinhua J. Song, Jinghua Xu, Zhulin Tan, Jonathan T. Reeves, Nelu Grinberg, Heewon Lee, Katie Kuzmich, Xuwu Feng, Nathan K. Yee, and Chris H. Senanayake
pp 534–538
Publication Date (Web): January 18, 2007 (Article)
DOI: 10.1021/op060211+

Efficient Asymmetric Synthesis of N-[(1R)-6-Chloro-2,3,4,9-tetrahydro-1H-carbazol-1-yl]-2-pyridinecarboxamide for Treatment of Human Papillomavirus Infections

Sharon D. Boggs, Jeremy D. Cobb, Kristjan S. Gudmundsson, Lynda A. Jones, Richard T. Matsuoka, Alan Millar, Daniel E. Patterson, Vicente Samano, Mark D. Trone, Shiping Xie, and Xiao-ming Zhou
pp 539–545
Publication Date (Web): February 14, 2007 (Article)
DOI: 10.1021/op060223v

Design, Development, and Scale-Up of a Selective meso-Epoxide Desymmetrization Process

David L. Varie, Christopher Beck, Sandra K. Borders, Molly D. Brady, Jason S. Cronin, Tracy K. Ditsworth, David A. Hay, David W. Hoard, Richard C. Hoying, Ryan J. Linder, Richard D. Miller, Eric D. Moher, Jacob R. Remacle, and John A. Rieck, IIIDavid D. Anderson, Paul N. Dodson, Mindy B. Forst, Duane A. Pierson, and Joseph A. Turpin
pp 546–559
Publication Date (Web): February 01, 2007 (Article)
DOI: 10.1021/op060225f

Optimized Catalytic Enantioselective Aryl Transfer Process Gives Access to mGlu2 Receptor Potentiators

Nicholas A. Magnus, Peter B. Anzeveno, D. Scott Coffey, David A. Hay, Michael E. Laurila, Jeffrey M. Schkeryantz, Bruce W. Shaw, and Michael A. Staszak
pp 560–567
Publication Date (Web): January 17, 2007 (Article)
DOI: 10.1021/op0602268

Development of Practical Rhodium Phosphine Catalysts for the Hydrogenation of β-Dehydroamino Acid Derivatives

Stephan Enthaler, Giulia Erre, Kathrin Junge, Jens Holz, Armin Börner, Elisabetta Alberico, Ilenia Nieddu, Serafino Gladiali, and Matthias Beller
pp 568–577
Publication Date (Web): December 30, 2006 (Article)
DOI: 10.1021/op0602270

Development of a Large Scale Asymmetric Synthesis of Vanilloid Receptor (TRPV1) Antagonist ABT-102

Kirill Lukin, Margaret C. Hsu, Gilles Chambournier, Brian Kotecki, C. J. Venkatramani, and M. Robert Leanna
pp 578–584
Publication Date (Web): February 23, 2007 (Article)
DOI: 10.1021/op060228s

A Mixed-Ligand Approach Enables the Asymmetric Hydrogenation of an α-Isopropylcinnamic Acid en Route to the Renin Inhibitor Aliskiren

Jeroen A. F. Boogers, Ulfried Felfer, Martina Kotthaus, Laurent Lefort, Gerhard Steinbauer, André H. M. de Vries, and Johannes G. de Vries
pp 585–591
Publication Date (Web): March 10, 2007 (Article)
DOI: 10.1021/op0602369

Solvent-Free Asymmetric Anhydride Opening in a Ball Mill

Toni Rantanen, Ingo Schiffers, and Carsten Bolm
pp 592–597
Publication Date (Web): February 10, 2007 (Article)
DOI: 10.1021/op6002743

Enantioselective Synthesis of Hydrobenzofuranones Using an Asymmetric Desymmetrizing Intramolecular Stetter Reaction of Cyclohexadienones

Qin Liu and Tomislav Rovis
pp 598–604
Publication Date (Web): March 22, 2007 (Article)
DOI: 10.1021/op600278f

Development of a Preparative-Scale Asymmetric Synthesis of (R)-p-Tolyl Methyl Sulfoxide for Use in a One-Pot Synthesis of a Drug Intermediate Containing a Trifluoromethyl-Substituted Alcohol Functionality

Zhengxu Han, Jinhua J. Song, Nathan K. Yee, Yibo Xu, Wenjun Tang, Jonathan T. Reeves, Zhulin Tan, Xiao-jun Wang, Bruce Lu, Dhileepkumar Krishnamurthy, and Chris H. Senanayake
pp 605–608
Publication Date (Web): April 17, 2007 (Article)
DOI: 10.1021/op700010a

Practical Syntheses of Chiral α-Amino Acids and Chiral Half-Esters by Kinetic Resolution of Urethane-Protected α-Amino Acid N-Carboxyanhydrides and Desymmetrization of Cyclic meso-Anhydrides with New Modified Cinchona Alkaloid Catalysts

Yutaka Ishii, Ryosuke Fujimoto, Masafumi Mikami, Satoshi Murakami, Yasushi Miki, and Yoshiro Furukawa
pp 609–615
Publication Date (Web): April 19, 2007 (Article)
DOI: 10.1021/op700023h

Catalytic, Enantioselective Synthesis of Taranabant, a Novel, Acyclic Cannabinoid-1 Receptor Inverse Agonist for the Treatment of Obesity

Cheng-yi Chen, Lisa F. Frey, Scott Shultz, Debra J. Wallace, Karen Marcantonio, Joeseph F. Payack, Enrique Vazquez, Shawn A. Springfield, George Zhou, Ping Liu, Gerard R. Kieczykowski, Alex M. Chen, Brian D. Phenix, Utpal Singh, Jeff Strine, Brianne Izzo, and Shane W. Krska
pp 616–623
Publication Date (Web): April 13, 2007 (Article)
DOI: 10.1021/op700026n

Communications to the Editor

Synthesis of 4-Fluoro-β-(4-fluorophenyl)-l-phenylalanine by an Asymmetric Phase-Transfer Catalyzed Alkylation:  Synthesis on Scale and Catalyst Stability

Daniel E. Patterson, Shiping Xie, Lynda A. Jones, Martin H. Osterhout, Christopher G. Henry, and Thomas D. Roper
pp 624–627
Publication Date (Web): November 20, 2006 (Article)
DOI: 10.1021/op060190j

Design of Chiral Phase Transfer Catalyst with Conformationally Fixed Biphenyl Core:  Application to Asymmetric Alkylation of Glycine Derivatives

Yong-Gang Wang and Keiji Maruoka
pp 628–632
Publication Date (Web): February 13, 2007 (Communication to Editor)
DOI: 10.1021/op0602324

Enantioselective Reduction of Nitroalkene Mixtures by in Situ Equilibration

Constantin Czekelius and Erick M. Carreira
pp 633–636
Publication Date (Web): April 06, 2007 (Communication to Editor)
DOI: 10.1021/op700029m

A Practical and Scaleable Synthesis of 1R,5S-Bicyclo[3.1.0]hexan-2-one:  The Development of a Catalytic Lithium 2,2,6,6-Tetramethylpiperidide (LTMP) Mediated Intramolecular Cyclopropanation of (R)-1,2-Epoxyhex-5-ene

Anthony D. Alorati, Matthew M. Bio, Karel M. J. Brands, Ed Cleator, Antony J. Davies, Robert D. Wilson, and Chris S. Wise
pp 637–641
Publication Date (Web): April 18, 2007 (Communication to Editor)
DOI: 10.1021/op700042w

Technical Notes

Catalytic Racemisation of Chiral Amines and Application in Dynamic Kinetic Resolution

A. John Blacker, Matthew J. Stirling, and Michael I. Page
pp 642–648
Publication Date (Web): May 04, 2007 (Technical Note)
DOI: 10.1021/op060233w

Book Reviews

Polymorphism in the Pharmaceutical Industry Edited by R. Hilfiker. Wiley-VCH:  Weinheim. 2006. 414 + xix pp. £105. ISBN 3-527-31146-7.

p 649
Publication Date (Web): February 21, 2007 (Book Review)
DOI: 10.1021/op7000029

Fundamentals of Early Clinical Drug Development:  From Synthesis Design to Formulation Edited by A. F. Abdel-Magid and S. Caron. Wiley:  New Jersey. 2006. 323 pp. £58.95. ISBN 0-471-69278-6.

pp 649–650
Publication Date (Web): February 17, 2007 (Book Review)
DOI: 10.1021/op7000035

Handbook of Industrial Biocatalysis Edited by Ching T. Hou. CRC/Taylor & Francis:  Boca Raton, FL. 2005. 557 pp + xv. $179.95. ISBN 0824724232.

p 650
Publication Date (Web): February 17, 2007 (Book Review)
DOI: 10.1021/op7000047
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