Enantioseparation of (RS)-Bupropion and determination of configuration

ABSTRACT

Racemate of (RS)-Bupropion (Bup) has been separated by derivatization approach and thin layer chromatography (TLC). It was extracted from commercially available tablets, purified, and characterized. A new chiral derivatization reagent (CDR) was synthesized by introducing L-leucine amide and butoxy group in cyanuric chloride (CC) moiety. Derivatization reaction was carried out using a two-fold molar excess of CDR under microwave irradiation (MWI). The diastereomeric pair was separated by TLC and the same were recovered by the preparative method; these were purified and characterized. Absolute configuration of the Bup moiety in the diastereomeric derivatives was confirmed by recording their ¹HNMR spectra and thus elution order was also established.

GRAPHICAL ABSTRACT

KEYWORDS:

• (RS)-Bupropion
• 1HNMR
• determination of configuration
• diastereomeric derivatives
• enantioseparation
• preparative TLC

Additional information

Funding

Thanks are due to Ms. Manisha Singh and Mr. Shiv Alwera (research fellows in the laboratory of RB) for their help during the completion of this work. Authors are thankful to the CSIR of India for granting research fellowship to Poonam Malik.