Patents using

Cyclopentyl
methyl ether(CPME)
Ver. 1.0─1─CONT

1. Alkylation, Silylation

ENTS● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ●2. Reactions under Lewis acid Conditions● ● ● ●

4● ● ● ●5● ● ● ● ● ● ● ●6● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ●8

3. Reactions under Bronsted acid Conditions
4. Reaction with Base or Organometals
5. Oxidation/Reduction

6. Reactions with Transition Metal Catalyst● ● ●9● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ●10● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ●11

7. Reaction With Lipase
8. Polymerisation

9. Extraction/Crystallization
10. Others

3● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ●12● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ● ●

14

─2─

1. Alkylation, Silylation
1-1

Michael Addition

Nippon Soda Co., Ltd. JP2005-225810

1-2

Ammoniumu salt

Nichia Corporation, JP2010-70539

1-3

Arylation

Fushimi Pharmaceutical Co., Ltd., JP2006-117637, 117638

─3─

2. Reactions under Lewis acid Conditions
2-1

Asynmetric addition

2-2

Friedel-crafts

Adeka Corporation JP2009-292754

2-3Beckmann rearrangement

Ube Industries Ltd. JP2010-229042

Takasago International Corporation WO2004/078730

─4─

3. Reactions under Bronsted acid Conditions
3-1

Removal of t-Bu group

3-2

Salt formation

3-3

Cyclization

Daito Pharmacrutical Co., Ltd. JP2008-208068

India-IPCA Laboratories US2008/018866

Hodogaya Chemical Co.,Ltd., JP2007-63147

─5─

4. Reaction with Base or Organometals
4-1

Cyclization

Toray Fine Chemicals Co., Ltd. JP2005-112761

4-2

Wittig reaction

SHIONO KORYO KAISHA, LTD. JP2007-297286

4-3

Reformatsky reagent

4-4

MeLi

4-5

Carbamoylation

MEIJI SEIKA KAISHA, LTD. WO2006-109823

4-6

Grignard

Sumitomo Chemical Co., Ltd. WO2009-110406

Takeda Pharmaceutical Co., Ltd. JP2007-182454

Tosoh Finechem Corporation WO2007-007697

─6─

4-7

Grignard

Tosoh Finechem Corporation JP2008-231047

4-8

Grignard

Yamagata Prefecture JP2009-218568

4-9

Grignard

Nippon Syokubai Co., Ltd., JP2010-215569

4-10 N-Arylation

Ishihara Industry Co., Ltd., JP2009-242370

4-11 Grignard

Sumitomo Seika Chemicals Co., ltd., JP2011-157277

4-12 Grignard

Sumitomo Seika Chemicals Co., Ltd., JP2011-157278

─7─

5. Oxidation/Reduction
15--15

NaBH4 reduction5-2Reduction

Daiichi Sankyo Co., Ltd. WO2004/060851

Professor-Nagashima JP2006-282651

CPME

Y.94%

5-3

LiBH4 reduction

Bristol-Myers Squibb, US2009/0258866, US8, 044, 043

5-4

LiAlH4 reduction

Mitsubishi Tanabe Pharma Corporation, WO2010/114179

─8─

6. Reactions with Transition Metal Catalyst
6-1

Tamao-Kumada Coupling

6-2

Heck Carbonylation

6-3

Tamao-Kumada Coupling

Sumitomo Seika Chemicals Co., Ltd., JP2009-155318

6-4

Tamao-Kumada Coupling

Sumitomo Seika Chemicals Co., Ltd., JP2010-53045

6-5

Cross-coupling

DE-Saltigo WO2008/151920

Tosoh F-Tech. Inc., JP2004-307488

Toyama Chemical Co., Ltd., JP2011-74072

─9─

7. Reaction With Lipase
7-1

Hydrolysis

Mitsubishi Gas Chemical Co., Inc., JP2009/278930

─ 10 ─

8. Polymerisation
8-1

Co-polymer

NOF Corporation, JP2008-214604

8-2

Co-polymer

AZ Electronic Materials USA Corp., US2010/119980

8-3

Co-polymer

JNC Corporation, JP2010-116464

8-4

Co-polymer

Shin-Etsu Chemical Co., Ltd., JP2011-213701

─ 11 ─

9. Extraction/Crystallization
9-1

Crystallization

9-2

Extraction

Taoka Chemical Co., Ltd., JP2009-185187

9-3

Extraction

Asahi Kasei Chemicals Corp., JP2010-229042

9-4Extraction

Daiichi Sankyo Co., Ltd. US2011/0257401

9-5

Crystallization

Eisai Co., Ltd., WO2006/121106

Toray Industries Inc., US2011/0272681

─ 12 ─

9-6

Crystallization & extraction

9-7

Crystallization

Konica Minolta Chemical Co., Ltd., JP2005-289836

9-8

Crystallization

Air Water Inc., JP2004-256434

Toray Industries Inc., JP2010-195745

─ 13 ─

10. Others
10-1 Bromination

Pﬁzer Inc., US2007/0219237

10-2 Cyclization

Hodogaya Chemical Co., Ltd., JP2007-63147

─ 14 ─

The information contained herein is believed to be reliable, but no representations, guarantees or warranties of any kind
are made as to its accuracy, suitability for particular applications or results to be obtained.
Please read the Safety Data Sheet (SDS) carefully prior to handling.
This product was developed for the application in this brochure. In case of other applications, please handle under yourconfirmation of safety for the applications, or please talk to Zeon Corporation beforehand.

─ 15 ─

Specialty Chemicals Division

1-6-2 Marunouchi, Chiyoda-ku, Tokyo 100-8246 Japan
Phone:+81-3-3216-0542 Fax:+81-3-3216-1303
http://www.zeon.co.jp

Sep. 2018
0918005(SE)Printed in Japan─ 16 ─

187.05-116-0104