Azobisisobutyronitrile → HCID 59066463, compound

Participants

Reaction Steps

A mixture of (±)-5-[(2Z)(1R*)-3-(4-fluorophenyl)-1-hydroxyprop-2-enyl](4R*,5R*)-1-methyl-4-phenylpyrrolidin-2-one (115 mg, 0.35 mmol), AIBN (10 mg, 0.06 mmol) and thiophenol (12 mg, 0.11 mmol) in benzene (10 mL) was heated at the reflux temperature for 4 h. The resulting mixture was concentrated under reduced pressure and purified by preparatory TLC (90% EtoAc/hex) to give (±)-(4R*,5R*)-5-[(2E)(1R*)-3-(4-fluorophenyl)-1-hydroxyprop-2-enyl]-1-methyl-4-phenylpyrrolidin-2-one (30 mg, 26%) as a white solid: mp 189-191° C.; 1H NMR (CDCl3) δ 2.49-2.57 (m, 1H), 2.98 (s, 3H), 3.12-3.21 (m, 1H), 3.84-3.89 (m, 2H), 4.09-4.14 (m, 1H), 6.07 (dd, J=16.2, 5.0 Hz, 1H), 6.40 (dd, J=16.2, 1.7 Hz, 1H), 6.97-7.03 (m, 2H), 7.21-7.42 (m, 7H).

Provenance & Evidence