Improved resolution of (+)-cis-2'-hydroxy-5,9-dimethyl-6,7-benzomorphan and preparation of racemic, (+)-, and (-)-cis-2-methylcyclopropyl-2'-hydroxy- 5,9-dimethyl-6,7-benzomorphan (cyclazocine)

Article abstract of DOI:10.1080/00397919908086216

We report novel procedures for the efficient resolution of (±)-cis-2'- hydroxy-5,9-dimethyl-6,7-benzomorphan via the (-)-N-acetyl-L-glutamate and (+)-α-bromocamphor-π-sulfonate salts, the direct N-substitution of the (+)- α-bromocamphor-π-sulfonate salts, and the use of these methods for the synthesis of racemic, (+)-, and (-)-cyclazocine.

Full text of DOI:10.1080/00397919908086216

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Synthetic Communications: An
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Improved Resolution of
(±)-cis-2′-Hydroxy-5,9-
dimethyl-6, 7-benzomorphan
and Preparation of
Racemic, (+)-, and (-)-
cis-2-Methylcyclopropyl-2′-
hydroxy-5,9-dimethyl-6,7-
benzomorphan (Cyclazocine)
William A. Boulanger a
a Albany Molecular Research, Inc., 21 Corporate
Circle, Albany, NY, 12203
Published online: 17 Sep 2007.
To cite this article: William A. Boulanger (1999) Improved Resolution of (±)-cis-2′-
Hydroxy-5,9-dimethyl-6, 7-benzomorphan and Preparation of Racemic, (+)-, and (-)-
cis-2-Methylcyclopropyl-2′-hydroxy-5,9-dimethyl-6,7-benzomorphan (Cyclazocine),
Synthetic Communications: An International Journal for Rapid Communication of
Synthetic Organic Chemistry, 29:12, 2201-2210, DOI: 10.1080/00397919908086216
To link to this article: http://dx.doi.org/10.1080/00397919908086216
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