Substrate Modification Approach to Achieve Efficient Resolution: Didesmethylcitalopram: A Key Intermediate for Escitalopram
Chandrashekar R Elati
1
,
Naveenkumar Kolla
1
,
Pravinchandra J Vankawala
1
,
Srinivas Gangula
1
,
Subrahmanyeswarara Chalamala
1
,
Sundaram Venkatraman
1
,
Bhattacharya Apurba
1
,
Vurimidi Himabindu
1
,
Vijayavitthal T. Mathad
1
1
Department of Research and Development, Dr. Reddy's Laboratories Ltd., IPD, Unit-III, Bollaram, Hyderabad - 502325, Andhrapradesh, India, and Institute of Science and Technology, J. N. T. University, Kukatpally, Hyderabad - 500072, Andhrapradesh, India
|
Publication type: Journal Article
Publication date: 2007-01-17
scimago Q1
wos Q1
SJR: 0.865
CiteScore: 5.4
Impact factor: 3.5
ISSN: 10836160, 1520586X
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
Research work presented here describes an approach to achieve the enantiopure escitalopram (1) via didesmethyl escitalopram (4), which is easily resolvable compared to citalopram (1a) through diastereomeric salt crystallization. The resolved intermediate (didesmethylcitalopram) was subsequently used for the preparation of the desired drug. This simple modification of the substrate makes a remarkable difference in the chemical resolution process. The first resolution of didesmethylcitalopram (±)-4 to furnish (+)-4, a novel key intermediate to assemble escitalopram (1) was achieved via diastereomeric salt resolution using (−)-di-p-toluoyltartaric acid (DPTTA). The resolution conditions were optimized; a key feature of this process is the addition of specific quantity of water at a specific temperature to the reaction mixture.
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Citations from 2024:
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GOST
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Elati C. R. et al. Substrate Modification Approach to Achieve Efficient Resolution: Didesmethylcitalopram: A Key Intermediate for Escitalopram // Organic Process Research and Development. 2007. Vol. 11. No. 2. pp. 289-292.
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Elati C. R., Kolla N., Vankawala P. J., Gangula S., Chalamala S., Venkatraman S., Apurba B., Himabindu V., Mathad V. T. Substrate Modification Approach to Achieve Efficient Resolution: Didesmethylcitalopram: A Key Intermediate for Escitalopram // Organic Process Research and Development. 2007. Vol. 11. No. 2. pp. 289-292.
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RIS
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TY - JOUR
DO - 10.1021/op060175e
UR - https://doi.org/10.1021/op060175e
TI - Substrate Modification Approach to Achieve Efficient Resolution: Didesmethylcitalopram: A Key Intermediate for Escitalopram
T2 - Organic Process Research and Development
AU - Elati, Chandrashekar R
AU - Kolla, Naveenkumar
AU - Vankawala, Pravinchandra J
AU - Gangula, Srinivas
AU - Chalamala, Subrahmanyeswarara
AU - Venkatraman, Sundaram
AU - Apurba, Bhattacharya
AU - Himabindu, Vurimidi
AU - Mathad, Vijayavitthal T.
PY - 2007
DA - 2007/01/17
PB - American Chemical Society (ACS)
SP - 289-292
IS - 2
VL - 11
SN - 1083-6160
SN - 1520-586X
ER -
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BibTex (up to 50 authors)
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@article{2007_Elati,
author = {Chandrashekar R Elati and Naveenkumar Kolla and Pravinchandra J Vankawala and Srinivas Gangula and Subrahmanyeswarara Chalamala and Sundaram Venkatraman and Bhattacharya Apurba and Vurimidi Himabindu and Vijayavitthal T. Mathad},
title = {Substrate Modification Approach to Achieve Efficient Resolution: Didesmethylcitalopram: A Key Intermediate for Escitalopram},
journal = {Organic Process Research and Development},
year = {2007},
volume = {11},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://doi.org/10.1021/op060175e},
number = {2},
pages = {289--292},
doi = {10.1021/op060175e}
}
Cite this
MLA
Copy
Elati, Chandrashekar R., et al. “Substrate Modification Approach to Achieve Efficient Resolution: Didesmethylcitalopram: A Key Intermediate for Escitalopram.” Organic Process Research and Development, vol. 11, no. 2, Jan. 2007, pp. 289-292. https://doi.org/10.1021/op060175e.