An Efficient Process of Racemization of 3-(Carbamoylmethyl)-5-methylhexanoic acid: A Pregabalin Intermediate
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Emcure Pharmaceuticals Ltd, R & D Centre, Plot No.12/2, F-II Block, M.I.D.C., Pimpri, Pune - 411018, India
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Тип публикации: Journal Article
Дата публикации: 2009-05-18
scimago Q1
wos Q1
БС1
SJR: 0.865
CiteScore: 5.4
Impact factor: 3.5
ISSN: 10836160, 1520586X
Organic Chemistry
Physical and Theoretical Chemistry
Краткое описание
A simple and cost-effective process for racemization of undesired (S)-3-(carbamoylmethyl)-5-methylhexanoic acid (9), produced during the resolution step, is described. The literature procedure is fraught with many difficulties including number of steps and hazardous reagents. We have developed a one pot process for the above-mentioned racemization of S-enantiomer. The basic objective is to convert S-enantiomer into the symmetrical glutarimide derivative followed by hydrolysis with an alkali. The transformation of 9 into glutarimide derivative (10) has been achieved with piperidine in refluxing toluene.
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Chavan A. B., Maikap G. C., Gurjar M. K. An Efficient Process of Racemization of 3-(Carbamoylmethyl)-5-methylhexanoic acid: A Pregabalin Intermediate // Organic Process Research and Development. 2009. Vol. 13. No. 4. pp. 812-814.
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Chavan A. B., Maikap G. C., Gurjar M. K. An Efficient Process of Racemization of 3-(Carbamoylmethyl)-5-methylhexanoic acid: A Pregabalin Intermediate // Organic Process Research and Development. 2009. Vol. 13. No. 4. pp. 812-814.
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TY - JOUR
DO - 10.1021/op900064x
UR - https://doi.org/10.1021/op900064x
TI - An Efficient Process of Racemization of 3-(Carbamoylmethyl)-5-methylhexanoic acid: A Pregabalin Intermediate
T2 - Organic Process Research and Development
AU - Chavan, Anil B
AU - Maikap, Golak C.
AU - Gurjar, Mukund K.
PY - 2009
DA - 2009/05/18
PB - American Chemical Society (ACS)
SP - 812-814
IS - 4
VL - 13
SN - 1083-6160
SN - 1520-586X
ER -
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@article{2009_Chavan,
author = {Anil B Chavan and Golak C. Maikap and Mukund K. Gurjar},
title = {An Efficient Process of Racemization of 3-(Carbamoylmethyl)-5-methylhexanoic acid: A Pregabalin Intermediate},
journal = {Organic Process Research and Development},
year = {2009},
volume = {13},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/op900064x},
number = {4},
pages = {812--814},
doi = {10.1021/op900064x}
}
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Chavan, Anil B., et al. “An Efficient Process of Racemization of 3-(Carbamoylmethyl)-5-methylhexanoic acid: A Pregabalin Intermediate.” Organic Process Research and Development, vol. 13, no. 4, May. 2009, pp. 812-814. https://doi.org/10.1021/op900064x.