Separation of Nadolol Stereoisomers by Chiral Liquid Chromatography at Analytical and Preparative Scales

• Type: Article in International Scientific Journal
• Date: 2013

Authors

Ribeiro, AE (Author) Other; Alírio Rodrigues (Author) FEUP; Pais, LS (Author) Other

Journal

Title: Chirality

Vol. 25

Pages: 197-205

ISSN: 0899-0042

Publisher: Wiley-Blackwell

Indexing

ISI Web of Knowledge - 3 Citations

Scopus - 1 Citation

Other information

Authenticus ID: P-002-025

DOI: 10.1002/chir.22132

Abstract (EN): The separation of the four nadolol stereoisomers on Chiralpak (R) AD by chiral liquid chromatography was carried out at both analytical and preparative scales. A screening of possible mobile-phase compositions was performed using different alcoholhydrocarbon mixtures. The results obtained confirm the use of 20:80:0.3 ethanol-hexane-diethylamine reported by McCarthy (1994) but introduce other possibilities for the complete resolution of the four nadolol stereoisomers at analytical scale, namely, the mixtures 3040:7060:0.3 ethanol-heptane-diethylamine. Additionally, this work describes how retention and resolution depend on the ethanol content in hexane and heptane mixtures. The separation of nadolol stereoisomers is also carried out at preparative scale and different alcoholhydrocarbon compositions are proposed, depending on the target component to be obtained. Particularly, this work presents the experimental separation of the more retained nadolol stereoisomer (RSR-nadolol) by simulated moving bed (SMB) chromatography using an 80:20:0.3 ethanol-heptane-diethylamine mobile phase. For a 2 g/l feed concentration, RSR-nadolol is 100% recovered at the extract outlet stream, 100% pure, and with a system productivity of 0.65 gRSR-nadolol/(lbed.h) and a solvent consumption of 9.6 lsolvent/gRSR-nadolol. Chirality 25:197205, 2013. (c) 2013 Wiley Periodicals, Inc.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 9