Phthalimide → HCID 86705491, compound

Participants

Reaction Steps

To a solution of 158 (3.45 g, 16.5 mmol) and THF (45 mL) cooled to 0° C. was added isoindoline-1,3-dione (2.67 g, 18.1 mmol) and PPh3 (6.49 g, 24.7 mmol) followed by the dropwise addition of neat DIAD (6.67 g, 33.0 mmol). The reaction was warmed to RT and stirred 18 h. The reaction was stirred with NaOH 2N (50 mL) and DCM (50 mL) for 2 h (emulsion) and then extracted with DCM. The combined organic fractions were dried (Na2SO4), filtered, and concentrated. The residue was triturated with hexane/EtOAc (1:1) and the precipitated POPh3 was filtered. The filtrate was concentrated and chromatographed (Isolera) eluting with hexane/EtOAc (9:1) to afford 2.05 g (32%) of (R)-2-(1-(3,4-dichlorophenyl)propyl)isoindoline-1,3-dione (160)

Provenance & Evidence