Enantiopure synthesis of 7-(1-pyrindanyl)propargyl ethers as rasagiline analogues via chemical or enzymatic resolution of 1-pyrindan-7-ol

• Type: Article in International Scientific Journal
• Date: 2015

Authors

Carlos A D Sousa (Author) Other; Ivo E Sampaio Dias (Author) Other; Fabio Rizzo Aguiar (Author) Other; Xerardo Garcia Mera (Author) Other; Jose E Rodriguez Borges (Author) FCUP

Journal

Title: RSC Advances

Vol. 5

Pages: 104509-104515

ISSN: 2046-2069

Publisher: Royal Society of Chemistry

Indexing

ISI Web of Knowledge - 8 Citations

Scopus - 8 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-00J-Z1S

DOI: 10.1039/c5ra24868j

Abstract (EN): In this work, the enantiopure synthesis of 7-(1-pyrindanyl) propargyl ethers - rasagiline analogues - via chemical and/or enzymatic resolution of the racemic precursor 1-pyrindan-7-ol is described. (R)-Methoxyphenylacetic acid - (R)-MPAA - and (S)-methoxyphenylacetic acid - (S)-MPAA were used as chemical resolution agents, whereas Candida antarctica lipase B (CALB) was employed as kinetic resolution catalyst. The enzymatic resolution was successfully achieved by two different approaches: (1) transesterification of racemic 1-pyrindan-7-ol, which was found to selectively acylate the (R)-enantiomer with high efficiency; (2) hydrolysis of the racemic 7-(1-pyrindanyl) acetate, which was also highly selective to the (R)-enantiomer. The enzymatic hydrolysis was performed in a non-aqueous solvent using a lipase with significant absorbed water content. The configuration of the two enantiomers of 1-pyrindan-7-ol (and consequently of the 7-(1-pyrindanyl) propargyl ethers) were unequivocally determined by X-ray crystallography and/or specific optical rotation.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 7