Studies on N-substituted nortropane derivatives,5

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  • Studies on N-Substituted Nortropane Derivatives. V. High-pressure Catalytic Hydrogenation of N-Substituted 3-Nortropanones and their Methiodides.

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High-pressure catalytic hydrogenation of N-substituted 3-nortropanones reported in Part I of this series and also of their methiodides was examined. In the case of tertiary amines, only the corresponding 3α-ols were obtained as the main product and the influence of N-substituents was not observed. Before the reduction of methiodides, the necessary infrared spectra were measured in order to establish the purity of the products and recovered materials. In reduction of methiodides, the more bulky the N-substituent became, the smaller did the amounts of 3α-ol methiodides. The possibility of a steric hindrance by fixed Na (piperidine side) substituents in the reduction was discussed.

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