Synthesis and Analgetic Activities of Some Aminobenzylcyclanols Derived from MenthoneÖzarslan, 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.
(Used TFSE for this one too, and couldn't find it. Hoping it's not hidden somewhere deep inside the hive...)