Hydrochloric Acid → 1-(1-Azabicyclo[3.1.1]heptan-5-yl)ethanone

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Reaction Steps

A solution of methyl 1-azabicyclo[3.1.1]hept-5-ylcarboxylate (D4, 1.12 g, 0.0072 mole) in methanol (5 ml) was treated with a solution of lithium hydroxide monohydrate (308 mg, 0.0073 mole) in water (20 ml) and the resulting solution stirred at room temperature for 20 h, then concentrated in vacuo to leave a white solid which was dried thoroughly. A stirred suspension of this product in dry THF (120 ml) under nitrogen was treated at room temperature with 1M methyllithium in ether (8.0 ml, 0.0080 mole) and then heated under reflux for 3.5 h. The mixture was allowed to cool, then poured into excess well stirred cold 1M hydrochloric acid. The resulting solution was basified to saturation point with potassium carbonate and extracted with ethyl acetate (1×100 ml), followed by chloroform (2×60 ml). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give the title compound (D 16) as a yellow oil (360 mg, 36%). This material was used without further purification.

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