volume 45 issue 23 pages 2676-2682

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 typeJournal Article
Publication date2015-08-24
scimago Q3
wos Q3
SJR0.322
CiteScore4.3
Impact factor1.8
ISSN00397911, 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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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.
GOST all authors (up to 50) Copy
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.
RIS |
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RIS Copy
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 -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@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}
}
MLA
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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.