Phthalimide → 2-(2-Phenyl-3-pyrrolidin-1-yl propyl)isoindole-1,3-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-phenyl-3-pyrrolidin-1-yl propan-1-ol (3.4 mmol) in THF (10 mL) is successively added phthalimide (4.1 mmol), triphenylphosphine (5.1 mmol) and diethyl azodicarboxylate (5.1 mmol) at 0° C., then the mixture is stirred at 0° C. for 1.5 h. After dilution with water, the mixture is acidified to pH<3 with aq. KHSO4 then washed with AcOEt. The aqueous layer basified to pH>11 with sat aq. NaHCO3 then extracted with AcOEt. The organic extracts are washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue is triturated with ether to give 2-(2-phenyl-3-pyrrolidin-1-yl propyl)isoindole-1,3-dione, which is directly used for the next reaction without further purification.

Provenance & Evidence