A short synthesis of d‐[1‐14C]‐serine of high enantiomeric purity. (27th February 2015)

• Record Type: Journal Article
• Authors: Song, Fengbin; Salter, Rhys; Weaner, Larry E.
• Is Part Of: Journal of labelled compounds & radiopharmaceuticals. Volume 58:Number 4(2015)
• Page Start: 173
• Page End: 176
• Publication Date: 2015-02-27
• Subjects: Tracers (Chemistry) -- Periodicals; Radiopharmaceuticals -- Periodicals; 615.8424
• DOI: 10.1002/jlcr.3272
• Languages: English
• ISSNs: 0362-4803

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>Herein, we report a short, three‐step synthesis of <sc>d</sc>‐[1‐¹⁴C]‐serine (4) in high enantiomeric purity. Starting from [¹⁴C]‐KCN and 2‐(benzyloxy)acetaldehyde, Strecker reaction using (<italic>R</italic>)‐1‐phenylethylamine as the chiral auxiliary gave two diastereomeric aminonitriles 1 and 2 in the ratio of 4:3, which were conveniently separated and purified chromatographically. Following hydrolysis and subsequent hydrogenolysis, the purified major diastereomer 1, was smoothly converted to <sc>d</sc>‐[1‐¹⁴C]‐serine (4) in an enantiomeric excess of &gt;99%, thus circumventing time intensive chiral HPLC enantiomeric resolution.</p> </abstract>