Phthalimide → HCID 71006879, compound

Participants

Reaction Steps

In an oven-dried 100 mL round-bottomed flask was dissolved tert-butyl (5S,6S,9S)-6-(2,3-difluorophenyl)-9-hydroxy-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-ylcarbamate (35.3 mg, 0.090 mmol) (9, azeotroped with dry benzene) in methylene chloride (3 mL) to give a colorless solution. isoindoline-1,3-dione (26.5 mg, 0.180 mmol) and triphenylphosphine (47.3 mg, 0.180 mmol) were added, followed by diisopropylazodicarboxylate (0.026 mL, 0.135 mmol). The mixture was stirred at rt under nitrogen. After 22 h, the mixture was directly subject to flash column chromatography up to 50% ethyl acetate/hexane afforded one major peak. Concentration afforded the desired product as a colorless oil. 1H NMR indicated that some elimination product might also be present. This was carried onto next reaction without further purification and characterization.

Provenance & Evidence