Phthalimide → 2-((2S)-2-(5-bromo-1-oxo-1,3-dihydro-2H-isoindol-2-yl)-3-{3-[(trimethylsilyl)ethynyl]-phenyl}propyl)-1H-isoindole-1,3(2H)-dione

Participants

Reaction Steps

To a solution of diisopropyl azodicarboxylate (0.35 mL, 1.8 mmol) in tetrahydrofuran (2.9 mL) was added 5-bromo-2-((1S)-2-hydroxy-1-{3-[(trimethylsilyl)ethynyl]benzyl}ethyl)-isoindolin-1-one (0.58 g, 1.3 mmol), phthalimide (0.21 g, 1.4 mmol), and triphenylphosphine (0.35 g, 1.3 mmol). The mixture was stirred at room temperature for 4 h. Direct purification by combi-flash chromatography eluting with 0-60% EtOAc in hexanes afforded the desired product. LC-MS found: 571.1 (M+H)+.

Provenance & Evidence