Phthalimide → HCID 57593205, compound

Participants

Reaction Conditions

Reaction Steps

A previous batch of the product from Step 8 (18) was combined with the above and 150 mg (0.48 mmol) of this crude material was dissolved in 3 ml of dry tetrahydrofuran then cooled to 0° C. Phthalimide 212 mg (1.4 mmol) was added to the cold solution followed by triphenylphosphine 189 mg (0.72 mmol) then DIAD 140 μl (0.72 mmol). The reaction mixture was stirred under nitrogen and allowed to warm to room temperature overnight. The solvent was evaporated and the solid redissolved in ethyl acetate then washed with saturated NaHCO3 and brine. The organic layer was then dried over MgSO4 and the solvent was removed in vacuo resulting in 700 mg of crude material that was purified by flash chromatography to give 95 mg (0.22 mmol, 44%) of 2-[1-(3-benzyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-2-yl)-2-methylpropyl]-1H-isoindole-1,3(2H)-dione (19) as a white solid.

Provenance & Evidence