ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

A convenient approach for vinylation reaction in the synthesis of 5-vinyl-2-pyrrolidinone, a key intermediate of vigabatrin

Kishore Karumanchi, Senthil Kumar Natarajan, Sunil Gadde, and Krishna Vanchanagiri

Chemical Research and Development, APL Research Centre-II, Aurobindo Pharma Ltd., Sangareddy District, India

E-mail: kkishore009@gmail.com

Received: 13 August 2019  Accepted: 10 December 2019

Abstract:

A convenient, safe and cost-effective method for carrying out the key vinylation of 5-ethoxy-2-pyrrolidinone (8) in the preparation of 5-vinyl-2-pyrrolidinone (2) in the presence of potassium carbonate is described. This present procedure is developed by replacing inherently hazardous ethyl magnesium bromide with inexpensive and eco-friendly potassium carbonate. The reaction was performed on a multi-gram scale, with vinyl magnesium bromide as the vinylation reagent, in an 81% yield to give the 5-vinyl-2-pyrrolidinone with excellent purity and without the need for chromatography.

Keywords: Vigabatrin; Anti epileptic drug; Potassium carbonate; 5-Vinyl-2-pyrrolidinone; Key intermediate

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-019-01030-2

Chemical Papers 74 (6) 2035–2039 (2020)