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Synthesis of 5‐,6‐, and 7‐deutero sparteines
Author(s) -
Meese Claus O.,
Ebner Thomas
Publication year - 1988
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.2580250312
Subject(s) - sparteine , chemistry , sodium borohydride , iminium , yield (engineering) , borohydride , medicinal chemistry , deuterium , sodium , stereochemistry , carbon atom , organic chemistry , catalysis , ring (chemistry) , materials science , physics , quantum mechanics , metallurgy
Kinetically controlled 1 H/ 2 H exchange at carbon atom 5 of (‐)‐1,6‐dehydrosparteinium monoperchlorate ( 3a ) followed by sodium borohydride or sodium borodeuteride reduction of the iminium double bond gave optically active 5,5‐( 2 H 2 )‐sparteine ( 1b ) and 5,5,6‐( 2 H 3 )‐sparteine ( 1c ), respectively. Under thermodynamic control a third deuterium atom was incorporated into 3 at carbon atom 7. Borohydride reduction or rapid re‐exchange followed by reduction lead to the novel sparteine analogues 5,5,7‐( 2 H 3 )‐sparteine ( 1d ) and 7‐( 2 H)‐sparteine ( 1e ). The title compounds have been prepared in 76 to 83 % yield and 89 to 97 % isotopic purity.