Phthalimide → (R)-tert-butyl 3-(1,3-dioxoisoindolin-2-yl)-3-(3-fluoro-4-(trifluoromethyl)phenyl)propylcarbamate

Participants

Reaction Steps

To a solution of 286 (0.600 g, 1.78 mmol) and THF (15 mL) cooled to 0° C. was added isoindoline-1,3-dione (0.288 g, 1.96 mmol) and PPh3 (0.700 g, 2.67 mmol) followed by the dropwise addition of a THF (6 mL) solution of DEAD (0.420 mL, 2.67 mmol). The reaction was warmed to RT and stirred for 20 h. The reaction was concentrated, triturated with ether and filtered. The resulting filtrate was poured into water and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with hexane/EtOAc (4:1) to afford 0.350 g (42.4%) of (R)-tert-butyl 3-(1,3-dioxoisoindolin-2-yl)-3-(3-fluoro-4-(trifluoromethyl)phenyl)propylcarbamate (288).

Provenance & Evidence