Synthesis and stereochemical assignment of exo- and endo-7-methyl-7-azabicyclo[2.2.1]heptan-2-ol

Authors
Ramanaiah, KCV Zhu, NJ Klein-Stevens, C Trudell, ML
Citation
Kcv. Ramanaiah et al., Synthesis and stereochemical assignment of exo- and endo-7-methyl-7-azabicyclo[2.2.1]heptan-2-ol, ORG LETT, 1(9), 1999, pp. 1439-1441
Citations number
12
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
9
Year of publication
1999
Pages
1439 - 1441
Database
ISI
SICI code
1523-7060(19991104)1:9<1439:SASAOE>2.0.ZU;2-B
Abstract
[GRAPHICS] The syntheses of both the exo and endo stereoisomers of 7-methyl-7-azabicyc lo[2.2.1]heptan-2-ol were achieved in straightforward fashion, Alternativel y, the intramolecular cyclization of syn-4-N-methylaminocyclohexane 1,2-epo xide was found to give exo-7-methyl-7-azabicyclo-[2,2,1]heptan-2-ol as the sole product. The stereochemistry of the exo isomer was unequivocally confi rmed by X-ray crystallography.