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Synthesis of tritium labelled (R) and (S)‐3‐aminoquinuclidine: A ubiquitous component of serotonin receptor ligands, part I
Author(s) -
Masjedizadeh Mohammad R.,
Parnes Howard
Publication year - 1996
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/(sici)1099-1344(199601)38:1<41::aid-jlcr811>3.0.co;2-n
Subject(s) - chemistry , tritium , enantiomer , amide , methanol , dimer , isocyanate , hydrolysis , tritium illumination , stereochemistry , nuclear chemistry , organic chemistry , physics , nuclear physics , polyurethane
(R) and (S)‐3‐aminoquinuclidines‐ 3 H with the specific activity of 35 Ci/mmol were prepared. Reduction of enamide 2 with carrier free tritium gas over RhCODCI dimer, (2S, 3S) Chiraphos in methanol gave racemic amide 9c . Hydrolysis followed by resolution of the enantiomers with (R)‐methyl benzyl isocyanate gave (R) and (S)‐3‐aminoquinuclidine‐ 3 H 10c‐S and 10c‐R . The enantiopurity purity of both isomers was >99.5%.