Methyl iodide → Methyl 2-(4-phenylbicyclo[2.2.2]oct-1-yl)propanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (0.9 mL, 6.39 mmol) in anhydrous THF (10 mL) cooled to −78° C. (CO2/acetone) was added nBuLi (2M solution in cyclohexane; 3.2 mL, 6.4 mmol) and the reaction mixture was allowed to stir at −78° C. for 5 mins. Methyl (4-phenylbicyclo[2.2.2]oct-1-yl)acetate (Intermediate 1(ii); 1.5 g, 5.81 mmol) in anhydrous THF (2 mL) was added and the mixture immediately became dark brown/black. It was allowed to stir for ˜30 mins at −78° C. then methyl iodide (0.4 mL, 6.39 mmol) was added and the reaction mixture was allowed to warm to ambient temperature over 4 hrs. Saturated aqueous ammonium chloride solution (50 mL) was added and the mixture extracted into EtOAc (2×150 mL), the organic extracts were combined, dried (MgSO4) and concentrated to leave crude product which was an inseparable mixture of the title compound and starting material which was taken directly through to the next stage without further characterisation.

Provenance & Evidence