Phthalimide → HCID 86705526, compound

Participants

Reaction Steps

To a solution of 262 (0.98 g, 2.91 mmol) and THF (30 mL) cooled to 0° C. was added sequentially isoindoline-1,3-dione (0.470 g, 3.20 mmol) and PPh3 (1.14 g, 4.36 mmol), followed by a solution of DEAD (1.72 mL, 4.36 mmol) and THF (10 mL). The reaction was warmed to RT and stirred overnight. The reaction was concentrated to dryness, Et2O (300 mL) added and the resulting solid was filtered and discarded. The filtrate was then 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 DCM:MeOH (500:2) to afford 0.99 g (73.1%) of (S)-tert-butyl 2-(1,3-dioxoisoindolin-2-yl)-2-(3-fluoro-4-(trifluoromethyl)phenyl)ethyl(methyl)carbamate (264).

Provenance & Evidence