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. 2018 Aug 31;23(9):2206. doi: 10.3390/molecules23092206

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© 2018 by the authors.

Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).

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Scheme 6 — Previously reported transformations of (R)-lactone 4 into brivaracetam (1). Reagents and Conditions: (i) SOCl₂, ZnCl₂, 55 °C, 68%; (ii) (S)-2-aminobutanamide hydrochloride, PEG 400/CH₂Cl₂, −10 °C, KOH; (iii) 33% HBr in AcOH, 80 °C, 2 h, 81%; (iv) HCl, CH₃CH₂OH, 40 °C, 89%; (v) tetrabutylammonium iodide, (S)-2-aminobutanamide, Na₂CO₃, isopropylacetate; (vi) methyl-tert-buthyl ether; (vii) isopropylacetate.