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)

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-φ-sulfonate salts, the direct N-substitution of the (+)-α-bromocamphor-φ-sulfonate salts, and the use of these methods for the synthesis of racemic, (+)-, and (-)-cyclazocine.