Paper
Several transformations of 3-benzyl-9-carbethoxymethyl-3,9-diazabicyclo[3.3.1]nonane
Published Oct 1, 1970 · E. S. Nikit-skaya, L. Yakhontov
Chemistry of Heterocyclic Compounds
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Abstract
The transformations of 3-benzyl-9-carbethoxymethyl-3,9-diazabicyclo[3.3.1]nonane (I) were studied. The dichloride of 9-(β-chloroethyl)-3,9-diazabicyclo[3.3.1]nonane, which is readily cyclized in the basic form to 3,9-diazatricyclo[3.3.1.23,9]undecane (V), was synthesized by reduction of I with LiAlH4 and debenzylation with subsequent replacement of the hydroxy group, in the alcohol formed, by chlorine. An unusual cleavage of the carboxymethyl residue to form the nitrogen-unsubstituted dichloride of 3,9-diazabicyclo[3.3.1]nonane (XI) occurs on treatment with thionyl chloride of the acid obtained by saponification and debenzylation of I.
This study demonstrates that 3-benzyl-9-carbethoxymethyl-3,9-diazabicyclo[3.3.1]nonane can be transformed into various compounds, including the nitrogen-unsubstituted dichloride of 3,9-diazabicyclo[3.3.1]non
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