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Synthesis and Stereochemistry of 7,9‐Disubstituted 3‐Azabicyclo[3.3.1]nonanes
Author(s) -
Nemes Peter,
Janke Frank,
Scheiber Pál
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199319930132
Subject(s) - chemistry , sodium methoxide , epimer , enamine , stereochemistry , molecule , enantiomer , organic chemistry , methanol , catalysis
The azabicyclic endo compound 3 was synthesized by reaction of enamine 1 with 2‐benzoyl‐1,3‐dichloropropane ( 2 ). The thermodynamically more stable exo isomer 4 was obtained by epimerization of 3 with sodium methoxide. The reduction of 3 and 4 was carried out with different reducing agents. The syn / anti isomeric amino alcohols 7a / 7b and 8a / 8b were separated either by fractional crystallization of their fumarate salts or by column chromatography. The relative configurations at C‐7 and C‐9 and the conformations of the molecules were determined by chemical and/or NMR spectroscopic methods.