The mixture of the sec. amine (IVa) and the tert. amine (IVb) is easily separated by treatment with ethyl chloroformate (III) leading to (IVb)·HCl and the soluble ester (IVc) (no yield given) which is reduced to (IVd).
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Title
The Nitrogen Inversion Barrier of 7‐Methyl‐7‐azabicyclo(2.2.1)heptane (IVd) and the “Bicyclic Effect”