Reduce the exocyclic vinyl group to ethyl while keeping the endocyclic norbornene double bond intact.

The strained endocyclic C=C of norbornene is usually the more reactive of the two toward catalytic hydrogenation, so standard catalysts affect the endocyclic double bond first or both at once. The selectivity needs to be inverted.

Add a secondary amine with aliphatic or aromatic substituents across the vinyl group of 2-vinylnorbornane to give the linear 2-(2-aminoethyl)norbornane.

The vinyl group is unactivated, the amine is secondary. So the target is the linear, anti-Markovnikov isomer — a combination that remains difficult for most known hydroamination catalysts.