Twisted Amide Reduction under Wolff−Kishner Conditions: Synthesis of a Benzo-1-Aza-Adamantane Derivative

A synthesis of 4,5-benzo-1-aza-tricyclo[4.3.1.13,8]undecane (1), a benzo-1-aza-adamantane
derivative, is described and features a previously unknown application of the Wolff−Kishner reduction of
a nonresonance stabilized or “twisted” amide. An intermediate amino ester is converted to a severely “twisted
amide”, which, when exposed to hydrazine in alcohol, provides the corresponding “twisted” amino hydrazone.
Wolff−Kishner conditions (KOH/ethylene glycol, 200 °C) provide the reduced target 1 without hydrolysis to
amino acid derivatives. These operations are conveniently performed in a single flask in high yield.