Molbank, Vol. 2018, Article M992: 1-Adamantylamidoxime (Molbank)

The title compound was prepared by the nucleophilic addition of hydroxylamine over 1-cyanoadamantane. The poor reactivity of the nitrile substrate, due to its scarcely electrophilic nature, prompted the need to employ several activating conditions. Energy supply via conventional heating, ultrasound, and microwave irradiation did not lead to product formation. Therefore, Lewis acid catalysis was attempted. Initial tests with ZnCl2 led to product formation in poor yields. Conversely, the use of AlCl3 led to the formation of the desired amidoxime in the moderate yield, which was further increased to an excellent yield by performing the reaction in a more concentrated medium. The structural identity of the title compound was proven by spectroscopic methods (IR, NMR). This compound was later employed as a starting material for the synthesis of 3,5-disubstituted 1,2,4-oxadiazole derivatives as potential 11?-HSD1 inhibitors.