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RR033E 20140620 www.TCIchemicals.com 800-423-8616 / 503-283-1681 888-520-1075 / 503-283-1987 Tel : Fax : [email protected] E-mail : Tel : +32 (0)3 735 07 00 Fax : +32 (0)3 735 07 01 E-mail : [email protected] Tel : +49 (0)6196 64053-00 Fax : +49 (0)6196 64053-01 E-mail : [email protected] Tel : +44 (0)1865 784560 Fax : +44 (0)1865 784561 E-mail : [email protected] Tel : 1800 425 7889 / 044-2262 0909 Fax : 044-2262 8902 E-mail : [email protected] Tel : +81 (0)3-5640-8878 Fax : +81 (0)3-5640-8902 E-mail : [email protected] Tel : 800-988-0390 / 021-67121386 Fax : 021-6712-1385 E-mail : [email protected] Ordering and Customer Service [email protected] E-mail : Tel : 800-423-8616 Fax : 888-520-1075 Availability, price or specification of the listed products are subject to change without prior notice. Reproduction forbidden without the prior written consent of Tokyo Chemical Industry Co., Ltd. Ruthenium Complex Catalysts for Hydrogenation of Esters to Alcohols New R0136 Ru-MACHO® 200mg / 1g R0137 Ru-MACHO®-BH 200mg / 1g These products were merchandized under the technical tie-up with TAKASAGO INTERNATIONAL CORPORATION. Ru-MACHO® is a registered trademark of TAKASAGO INTERNATIONAL CORPORATION. N P P Ru H Cl CO Ph Ph H Ph Ph W. Kuriyama et al., Org. Process Res. Dev. 2012, 16, 166. Alcohol Ester R0136 (0.1 mol%) H 2 (5 MPa) NaOMe (0.1 eq.) MeOH, 16 h From the technical document of TAKASAGO INTERNATIONAL CORPORATION Alcohol Ester R0137 (0.1 mol%) H 2 (5 MPa) THF, 80 °C, 16 h Ru-MACHO® [R0136] Ru-MACHO®-BH [R0137] N P P Ru H H CO Ph Ph H BH 3 Ph Ph Substrate Product Yield (%) CO 2 Me CH 2 OH 90 92 98* BnO CO 2 Me BnO CH 2 OH CO 2 Me CH 2 OH N N CH 2 OH CO 2 Me 86 *neat, 150 °C, 2 h Substrate Product Yield (%) 77 78 93 88 O NHCbz O OH HO NHCbz O O CO 2 Me CO 2 Me O O CH 2 OH CH 2 OH Ph CO 2 Me Ph CH 2 OH CO 2 Me NHBoc CH 2 OH NHBoc ee (%) ee (%) = (% ee of Substrate) - (% ee of Product) <1 <1 <1 2 Advantages Reaction Examples ɾ Catalyze the Hydrogenation of Esters to Alcohols ɾ The Reaction Proceeds in Various Solvents (neat, methanol, THF, etc.) ɾ It Can Reduce Sterically-bulky Substrates because of its Heat Stability ɾ The Addition of Base is Unnecessary by Using R0137

Ru-MACHO® Ru-MACHO®-BH [R0136] - TCI Chemicals Ru-MACHO® 200mg / 1g R0137 Ru-MACHO®-BH 200mg / 1g These products were merchandized under the technical tie-up with TAKASAGO INTERNATIONAL

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Page 1: Ru-MACHO® Ru-MACHO®-BH [R0136] - TCI Chemicals Ru-MACHO® 200mg / 1g R0137 Ru-MACHO®-BH 200mg / 1g These products were merchandized under the technical tie-up with TAKASAGO INTERNATIONAL

RR033E 20140620www.TCIchemicals.com

800-423-8616 / 503-283-1681888-520-1075 / 503-283-1987

Tel : Fax :

[email protected] :

Tel : +32 (0)3 735 07 00Fax : +32 (0)3 735 07 01E-mail : [email protected]

Tel : +49 (0)6196 64053-00Fax : +49 (0)6196 64053-01E-mail : [email protected]

Tel : +44 (0)1865 784560Fax : +44 (0)1865 784561E-mail : [email protected]

Tel : 1800 425 7889 / 044-2262 0909Fax : 044-2262 8902E-mail : [email protected]

Tel : +81 (0)3-5640-8878 Fax : +81 (0)3-5640-8902E-mail : [email protected]

Tel : 800-988-0390 / 021-67121386Fax : 021-6712-1385E-mail : [email protected]

Ordering and Customer Service

[email protected] :

Tel : 800-423-8616Fax : 888-520-1075

Availability, price or speci�cation of the listed products are subject to change without prior notice. Reproduction forbidden without the prior written consent of Tokyo Chemical Industry Co., Ltd.

Ruthenium Complex Catalysts for Hydrogenation of Esters to Alcohols

New

R0136 Ru-MACHO® 200mg / 1gR0137 Ru-MACHO®-BH 200mg / 1g

These products were merchandized under the technical tie-up with TAKASAGO INTERNATIONAL CORPORATION. Ru-MACHO® is a registered trademark of TAKASAGO INTERNATIONAL CORPORATION.

N P

PRu

H

Cl COPh

Ph

HPhPh

W. Kuriyama et al., Org. Process Res. Dev. 2012, 16, 166.

AlcoholEster

R0136 (0.1 mol%)H2 (5 MPa)

NaOMe (0.1 eq.)

MeOH, 16 h

From the technical document of TAKASAGO INTERNATIONAL CORPORATION

AlcoholEster

R0137 (0.1 mol%)H2 (5 MPa)

THF, 80 °C, 16 h

Ru-MACHO®[R0136]

Ru-MACHO®-BH[R0137]

N P

PRu

H

H COPh

Ph

H

BH3

PhPh

Substrate

Product

Yield (%)

CO2Me

CH2OH

90 92 98*

BnO CO2Me

BnO CH2OH

CO2Me

CH2OH

N

N CH2OH

CO2Me

86

*neat, 150 °C, 2 h

Substrate

Product

Yield (%) 77 78 9388

O

NHCbz

O

OHHO

NHCbz

O

O

CO2Me

CO2MeO

O

CH2OH

CH2OH

PhCO2Me

PhCH2OH

CO2Me

NHBoc

CH2OH

NHBoc

ee (%)

ee (%) = (% ee of Substrate) - (% ee of Product)

<1 <1 <12

Advantages

Reaction Examples

・ Catalyze the Hydrogenation of Esters to Alcohols・ The Reaction Proceeds in Various Solvents (neat, methanol, THF, etc.)・ It Can Reduce Sterically-bulky Substrates because of its Heat Stability・ The Addition of Base is Unnecessary by Using R0137