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A short synthesis of d ‐[1‐ 14 C]‐serine of high enantiomeric purity
Author(s) -
Song Fengbin,
Salter Rhys,
Weaner Larry E.
Publication year - 2015
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3272
Subject(s) - chemistry , diastereomer , enantiomer , strecker amino acid synthesis , hydrogenolysis , enantiomeric excess , serine , hydrolysis , chiral auxiliary , acetaldehyde , chiral column chromatography , stereochemistry , high performance liquid chromatography , chromatography , organic chemistry , enantioselective synthesis , catalysis , enzyme , ethanol
Herein, we report a short, three‐step synthesis of d ‐[1‐ 14 C]‐serine (4) in high enantiomeric purity. Starting from [ 14 C]‐KCN and 2‐(benzyloxy)acetaldehyde, Strecker reaction using ( R )‐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 d ‐[1‐ 14 C]‐serine (4) in an enantiomeric excess of >99%, thus circumventing time intensive chiral HPLC enantiomeric resolution.