An Enantioselective Formal Synthesis of Montelukast Sodium
A formal synthesis of the antiasthma drug montelukast sodium is described, wherein the key chiral diol intermediate was accessed with greater convergence of the C–C bond-forming steps as compared to previous routes. Improved synthetic efficiency was achieved by deploying homogeneous metal-based cata...
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Published in | Journal of organic chemistry Vol. 80; no. 8; pp. 3891 - 3901 |
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Main Authors | , , , , , , , , , , , |
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17.04.2015
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Abstract | A formal synthesis of the antiasthma drug montelukast sodium is described, wherein the key chiral diol intermediate was accessed with greater convergence of the C–C bond-forming steps as compared to previous routes. Improved synthetic efficiency was achieved by deploying homogeneous metal-based catalysis in two pivotal steps. In the first, a tandem Mizoroki–Heck reaction and double-bond isomerization between a previously known allyl alcohol intermediate and a hindered 2-(2-halophenyl)propan-2-ol secured direct access to the 3-(2-(2-hydroxypropan-2-yl)phenyl)-1-phenylpropan-1-one moiety in the product. In the second step, asymmetric hydrogenation of the ketone functionality in the Mizoroki–Heck reaction product provided a convenient method to introduce the benzylic alcohol chiral center and obtain the desired chiral diol precursor of montelukast sodium. A detailed catalyst screening led to the identification of ((R)-Xyl-BINAP)((R,R)-DPEN)RuCl2 as a catalyst that afforded an enantioselectivity of 99% ee in the hydrogenation step on a multigram lab scale at a molar substrate:catalyst loading of 5000:1. |
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AbstractList | A formal synthesis of the antiasthma drug montelukast sodium is described, wherein the key chiral diol intermediate was accessed with greater convergence of the C-C bond-forming steps as compared to previous routes. Improved synthetic efficiency was achieved by deploying homogeneous metal-based catalysis in two pivotal steps. In the first, a tandem Mizoroki-Heck reaction and double-bond isomerization between a previously known allyl alcohol intermediate and a hindered 2-(2-halophenyl)propan-2-ol secured direct access to the 3-(2-(2-hydroxypropan-2-yl)phenyl)-1-phenylpropan-1-one moiety in the product. In the second step, asymmetric hydrogenation of the ketone functionality in the Mizoroki-Heck reaction product provided a convenient method to introduce the benzylic alcohol chiral center and obtain the desired chiral diol precursor of montelukast sodium. A detailed catalyst screening led to the identification of ((R)-Xyl-BINAP)((R,R)-DPEN)RuCl2 as a catalyst that afforded an enantioselectivity of 99% ee in the hydrogenation step on a multigram lab scale at a molar substrate:catalyst loading of 5000:1. A formal synthesis of the antiasthma drug montelukast sodium is described, wherein the key chiral diol intermediate was accessed with greater convergence of the CC bond-forming steps as compared to previous routes. Improved synthetic efficiency was achieved by deploying homogeneous metal-based catalysis in two pivotal steps. In the first, a tandem Mizoroki-Heck reaction and double-bond isomerization between a previously known allyl alcohol intermediate and a hindered 2-(2-halophenyl)propan-2-ol secured direct access to the 3-(2-(2-hydroxypropan-2-yl)phenyl)-1-phenylpropan-1-one moiety in the product. In the second step, asymmetric hydrogenation of the ketone functionality in the MizorokiHeck reaction product provided a convenient method to introduce the benzylic alcohol chiral center and obtain the desired chiral diol precursor of montelukast sodium. A detailed catalyst screening led to the identification of ((R)-Xyl-BINAP)((R,R)-DPEN)RuCl2 as a catalyst that afforded an enantioselectivity of 99% ee in the hydrogenation step on a multigram lab scale at a molar substrate:catalyst loading of 5000:1. A formal synthesis of the antiasthma drug montelukast sodium is described, wherein the key chiral diol intermediate was accessed with greater convergence of the C–C bond-forming steps as compared to previous routes. Improved synthetic efficiency was achieved by deploying homogeneous metal-based catalysis in two pivotal steps. In the first, a tandem Mizoroki–Heck reaction and double-bond isomerization between a previously known allyl alcohol intermediate and a hindered 2-(2-halophenyl)propan-2-ol secured direct access to the 3-(2-(2-hydroxypropan-2-yl)phenyl)-1-phenylpropan-1-one moiety in the product. In the second step, asymmetric hydrogenation of the ketone functionality in the Mizoroki–Heck reaction product provided a convenient method to introduce the benzylic alcohol chiral center and obtain the desired chiral diol precursor of montelukast sodium. A detailed catalyst screening led to the identification of ((R)-Xyl-BINAP)((R,R)-DPEN)RuCl2 as a catalyst that afforded an enantioselectivity of 99% ee in the hydrogenation step on a multigram lab scale at a molar substrate:catalyst loading of 5000:1. |
Author | Lloyd, Richard C Dahanukar, Vilas Hareshwar Kandirelli, Venkata Kiran Kumar Oruganti, Srinivas Bollikonda, Satyanarayana Chaplin, David A Mohanarangam, Saravanan Makthala, Laxman Fox, Martin E Jinna, Rajender Reddy Sen, Saikat Mahoney, Thomas |
AuthorAffiliation | Integrated Product Development Organization, Dr. Reddy’s Laboratories Ltd Chirotech Technology Centre, Dr. Reddy’s Laboratories (EU) Limited University of Hyderabad Campus Center for Process Research & Innovation, Dr. Reddy’s Institute of Life Sciences |
AuthorAffiliation_xml | – name: Integrated Product Development Organization, Dr. Reddy’s Laboratories Ltd – name: Chirotech Technology Centre, Dr. Reddy’s Laboratories (EU) Limited – name: Center for Process Research & Innovation, Dr. Reddy’s Institute of Life Sciences – name: University of Hyderabad Campus |
Author_xml | – sequence: 1 givenname: Satyanarayana surname: Bollikonda fullname: Bollikonda, Satyanarayana – sequence: 2 givenname: Saravanan surname: Mohanarangam fullname: Mohanarangam, Saravanan – sequence: 3 givenname: Rajender Reddy surname: Jinna fullname: Jinna, Rajender Reddy – sequence: 4 givenname: Venkata Kiran Kumar surname: Kandirelli fullname: Kandirelli, Venkata Kiran Kumar – sequence: 5 givenname: Laxman surname: Makthala fullname: Makthala, Laxman – sequence: 6 givenname: Saikat surname: Sen fullname: Sen, Saikat – sequence: 7 givenname: David A surname: Chaplin fullname: Chaplin, David A – sequence: 8 givenname: Richard C surname: Lloyd fullname: Lloyd, Richard C – sequence: 9 givenname: Thomas surname: Mahoney fullname: Mahoney, Thomas – sequence: 10 givenname: Vilas Hareshwar surname: Dahanukar fullname: Dahanukar, Vilas Hareshwar – sequence: 11 givenname: Srinivas surname: Oruganti fullname: Oruganti, Srinivas – sequence: 12 givenname: Martin E surname: Fox fullname: Fox, Martin E email: mfox@drreddys.com |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/25807000$$D View this record in MEDLINE/PubMed |
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Keywords | ANTAGONIST REDUCTION ALLYLIC ALCOHOLS ARYL HALIDES PALLADIUM-CATALYZED ARYLATION INTERMEDIATE ALDEHYDES ASYMMETRIC HYDROGENATION KETO ESTER EFFICIENT |
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Snippet | A formal synthesis of the antiasthma drug montelukast sodium is described, wherein the key chiral diol intermediate was accessed with greater convergence of... |
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SubjectTerms | Acetates - chemical synthesis Acetates - chemistry Anti-Asthmatic Agents - chemical synthesis Anti-Asthmatic Agents - chemistry Catalysis Chemistry Chemistry, Organic Coordination Complexes - chemistry Hydrogenation Molecular Structure Physical Sciences Quinolines - chemical synthesis Quinolines - chemistry Ruthenium - chemistry Science & Technology Sodium - chemistry Stereoisomerism |
Title | An Enantioselective Formal Synthesis of Montelukast Sodium |
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