Enantioselective Synthesis of ((1R,2R)-Cyclohexane-1,2-diyl)bis(methylene)dimethanesulfonate, a Lurasidone Hydrochloride Intermediate
Sharad S Pachore
1
,
T.V. Pratap
1
,
K. Umesh
1
,
Basaveswara Rao M V
2
,
C Murthy
3
,
M. Suresh Babu
1
1
Technology Development Centre, Custom Pharmaceutical Services, Dr Reddy's Laboratories Ltd, Miyapur,Hyderabad,India
|
2
Department of Chemistry, Krishna University, Machilipatnam, Andhra Pradesh, India
|
Publication type: Journal Article
Publication date: 2015-08-24
scimago Q3
wos Q3
SJR: 0.322
CiteScore: 4.3
Impact factor: 1.8
ISSN: 00397911, 15322432
Organic Chemistry
Abstract
AbstractA concise, economical, and highly enantioselective synthesis of bismesylate intermediate of lurasidone HCl, an antipsychotic, has been developed. The key steps involved in the synthesis are thionyl chloride–catalyzed esterification of tetrahydrophthalic anhydride in MeOH, epimerization of cis to trans isomer, hydrolysis of the diester, resolution of the diacid, reduction with Red-Al, and finally bismesylation of the corresponding diol, which provided the desired intermediate ((1 R,2 R)-cyclohexane-1,2-diyl)bis(methylene) dimethanesulfonate in overall good yield.
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Total citations:
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Citations from 2024:
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(71%)
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Ravi Ganesh K. et al. Enantioselective Synthesis of ((1R,2R)-Cyclohexane-1,2-diyl)bis(methylene)dimethanesulfonate, a Lurasidone Hydrochloride Intermediate // Synthetic Communications. 2015. Vol. 45. No. 23. pp. 2676-2682.
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Pachore S. S., Pratap T., Umesh K., M V B. R., Murthy C., Suresh Babu M. Enantioselective Synthesis of ((1R,2R)-Cyclohexane-1,2-diyl)bis(methylene)dimethanesulfonate, a Lurasidone Hydrochloride Intermediate // Synthetic Communications. 2015. Vol. 45. No. 23. pp. 2676-2682.
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RIS
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TY - JOUR
DO - 10.1080/00397911.2015.1074695
UR - https://doi.org/10.1080/00397911.2015.1074695
TI - Enantioselective Synthesis of ((1R,2R)-Cyclohexane-1,2-diyl)bis(methylene)dimethanesulfonate, a Lurasidone Hydrochloride Intermediate
T2 - Synthetic Communications
AU - Pachore, Sharad S
AU - Pratap, T.V.
AU - Umesh, K.
AU - M V, Basaveswara Rao
AU - Murthy, C
AU - Suresh Babu, M.
PY - 2015
DA - 2015/08/24
PB - Taylor & Francis
SP - 2676-2682
IS - 23
VL - 45
SN - 0039-7911
SN - 1532-2432
ER -
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BibTex (up to 50 authors)
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@article{2015_Ravi Ganesh,
author = {Sharad S Pachore and T.V. Pratap and K. Umesh and Basaveswara Rao M V and C Murthy and M. Suresh Babu},
title = {Enantioselective Synthesis of ((1R,2R)-Cyclohexane-1,2-diyl)bis(methylene)dimethanesulfonate, a Lurasidone Hydrochloride Intermediate},
journal = {Synthetic Communications},
year = {2015},
volume = {45},
publisher = {Taylor & Francis},
month = {aug},
url = {https://doi.org/10.1080/00397911.2015.1074695},
number = {23},
pages = {2676--2682},
doi = {10.1080/00397911.2015.1074695}
}
Cite this
MLA
Copy
Ravi Ganesh, K., et al. “Enantioselective Synthesis of ((1R,2R)-Cyclohexane-1,2-diyl)bis(methylene)dimethanesulfonate, a Lurasidone Hydrochloride Intermediate.” Synthetic Communications, vol. 45, no. 23, Aug. 2015, pp. 2676-2682. https://doi.org/10.1080/00397911.2015.1074695.