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

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.

1. concentrationconcentrated in vacuo
2. customto leave a white solid which
3. customwas dried thoroughly
4. additionA stirred suspension of this product in dry THF (120 ml) under nitrogen
5. temperatureheated
6. temperatureunder reflux for 3.5 h
7. temperatureto cool
8. extractionextracted with ethyl acetate (1×100 ml)
9. dry with materialThe combined extracts were dried (Na2SO4)
10. concentrationconcentrated in vacuo

ORD record

ord-1a7e729494634735953020f7e9161bb2

Source dataset

uspto-grants-1992_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05157160