2- and 5- substituted 5-amino-2,6,6-trimethyltetrahydropyrans.
Reaction of N,N-disubstituted 2-carboxyamido-2,6,6-trimethyltetrahydropyran-5-carboxylic acids with diphenyl phosphorazide in the presence of triethylamine and benzyl alcohol gave N,N-disubstituted 5-benzyloxycarbonylamino-2-carboxyamido-2,6,6-trimethyltetrahydr-pyrans, which in turn yielded N,-disubstituted 2-aminomethyl-5-methylamino-2,6,6-trimethyltetrahydropyrans by LiA1H4 reduction. 5-Benzyloxycarbonylamino-2-carboxypyrrolidino-2,6,6-trimethyltetrahydropyran gave 5-amino-2,6,6-trimethyl-2--pyrrolidinomethyltetrahydropyran by hydrogenolysis followed by LiA1H4 reduction. Among the amides prepared from the latter, the diphenylacetic acid amide showed antiarrhythmic and local-anesthetic activity.
D000577:Amides / Q000138:chemical synthesis; D000779:Anesthetics, Local / Q000138:chemical synthesis; D000818:Animals; D000889:Anti-Arrhythmia Agents / Q000138:chemical synthesis; D002264:Carboxylic Acids; D006168:Guinea Pigs; D007202:Indicators and Reagents; D051379:Mice; D011714:Pyrans / Q000138:chemical synthesis*
D000577:Amides; D000779:Anesthetics, Local; D000889:Anti-Arrhythmia Agents; D002264:Carboxylic Acids; D007202:Indicators and Reagents; D011714:Pyrans