Ammonia → 5-(Cyclooctyl-methyl)-spiro[indoline-3,4'-piperidin]-2-one

Participants

Reaction Conditions

Reaction Steps

To a magnetically stirred solution of liquid ammonia (10 mL) was added lithium (20 mg) at −78° C. under nitrogen atmosphere causing the solution to turn dark-blue. To the reaction mixture was then added a solution of 1-benzyl-5-(cyclooctyl-methyl)-spiro[indoline-3,4′-piperidin]-2-one (0.025 g, 0.06 mmol) in dry THF (2 mL). The reaction mixture was stirred −78° C. under nitrogen atmosphere for a few minutes, then ammonium chloride was added and the reaction mixture was stirred at room temperature for one hour. The reaction mixture was partitioned with water and ethyl acetate. The organic layer was washed with brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield the title compound as a foam.

Provenance & Evidence