AN EFFICIENT NOVEL RESOLUTION OF DESMETHYLCITALOPRAM / BROMO DESMETHYLCITALOPRAM BY USING DI-P-TOLUOYL-D-TARTARIC ACID: A KEY INTERMEDIATES FOR ESCITALOPRAM COMMERCIAL SYNTHESIS

2016-08-12T02-13-49Z
Source: Indo American Journal of Pharmaceutical Research
Narsihma Reddy Bobbali,, Garimella. K. A. S. S. Narayan,*, Ranjith kumar. S, Umar khan Mohammed, Muniprasad M., Mamatha Bobbali.
The present research work reported here covers an innovation approach to synthesis the enantiopure Escitalopram, a widely used anti-depressants by involving four-step process viz., (i) desmethyl reaction of Citalopram / bromo Citalopram. (ii) Resolution of desmethylcitalopram /bromo desmethylcitalopram using Di-p-toluoyl-D-Tartaric acid (DPTTA) in methanol, which is subsequently given novel key intermediates to eventually give Escitalopram by means of diastereomeric salt formation and further, optimized the novel resolution condition and other key factors. The most striking feature of this process in the addition of specific quantity of methanol and all the optimized parameters of the resolution process details are discussed. (iii) Isolation of Desmethyl Escitalopram / Bromo desmethylescitalopram (iv) This step pertains to enantiomerically pure desmethylescitalopram on alkylation with formaldehyde give active pharmaceutical ingredient 1 with good yield (75-78%) and quality. (v) Another enantiomerically pure Bromo desmethylescitalopram on alkylation with formaldehyde and formic acid, followed by cyanation affords 1 with good yield (~70%) and quality. In the present research study describes the commercially feasible new synthetic process of Escitalopram 1 by the novel resolution of desmethylcitalopram/ bromo desmethylcitalopram with good yield and quality of the product.


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