A short synthesis of d-[1-(14) C]-serine of high enantiomeric purity.
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.
Janssen Research & Development LLC, Janssen Pharmaceutical Companies of Johnson & Johnson, Welsh & McKean Roads, Spring House, PA, 19477-0776, USA.
Fengbin
F
Song
Rhys
R
Salter
Larry E
LE
Weaner
D002250:Carbon Radioisotopes / Q000737:chemistry*; D007553:Isotope Labeling / Q000379:methods*; D019275:Radiopharmaceuticals / Q000032:analysis* / Q000138:chemical synthesis*; D012694:Serine / Q000737:chemistry*; D013237:Stereoisomerism
D002250:Carbon Radioisotopes; D019275:Radiopharmaceuticals; D012694:Serine
carbon-14; d-[1-14C]-serine; high enantiomeric purity; radiosynthesis