Abstract
9-Amino-1-(m-hydroxyphenyl) bicyclo [3. 3. 1] nonanes (Va) and their seven-membered homologs (Vb) were synthesized as potential analgetic agents. Condensation of acryloyl chloride with the morpholine enamine of the cyclohexanone (1a) gave the diketone (4a). Ketalization of 4a followed by Wolff-Kishner reduction gave the 9-oxo derivative (11), which was converted to the 9-amino derivative (16) via the oxime (12). Condensation of acryloyl chloride and the morpholine enamine of the cycloheptanone (1b) gave the imminium salt (3b). Reaction of 3b with NH2OH occurred regiospecifically to give the 9-oxo-10-oxime (19). The oxime (19) was ultimately converted to the 10-amino derivative (27) via the amino-alcohol (21). LiAlH4 reduction of the 10-endo-ethoxycarbamoyl derivative (25) and its 9-hydroxy derivative (23) anomalously gave epimeric mixtures of the 10-methylamino derivatives. From the primary amines 16 and 27, various N-substituted derivatives were prepared for pharmacological evaluation. None showed significant activity.
