Synthesis and Analgetic Activities of Some Aminobenzylcyclanols Derived from Menthone
Özarslan, Ö. et al.
Arch. Pharm. (Weinheim) 327, 525-528 (1994)
Abstract:
Several cyclohexanamines such as Tilidin, Tramadol, and Ciramadol have been used as opiate analgesic drugs. Here, we describe synthesis and analgesic activity of some aminocyclanols from (-)-menthone (1R,4S-1-methyl-4-isopropyl-cyclohexan-3-one).
Two synthetic routes are described for the preparation of amino-benzylcyclanols and related derivates: One is the reaction of alpha-benzylcyclanols. In the other approach, benzisoxazols are first formed from benzylnitrones and cycloalkene, then treatment of benzisoxazoles with an allyl-halide produces the corresponding benzoxazoline halide and hydrogenolysis of these halides give the desired compounds.
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(Used TFSE for this one too, and couldn't find it. Hoping it's not hidden somewhere deep inside the hive...)