Water → 3-(Naphth-2-yl)-8-azabicyclo[3.2.1]octane oxalate

Participants

Reaction Steps

A mixture of 2.64 gm (8.53 mMol) 3-(naphth-2-yl)-8-ethoxycarbonyl-8-azabicyclo[3.2.1]octane, 2.14 gm (42.7 mMol) hydrazine hydrate, and 2.87 gm (51.2 mMol) potassium hydroxide in 70 mL ethylene glycol was heated at reflux for 2 hours. The reaction mixture was allowed to cool gradually to room temperature, poured into water and extracted well with diethyl ether. The organic phase was dried over sodium sulfate and concentrated under reduced pressure. The residue was treated with oxalic acid to provide the title compound.

Provenance & Evidence