Phthalimide → 2-[(1S)-3-Chloro-1-Phenylpropyl]-1H-Isoindole-1,3(2H)-Dione

Participants

Reaction Steps

Prepared according to the general procedure described in Srebnik, M.; Ramachandran, P. V.; Brown, H. C. J. Org. Chem. 1988, 53, 2916–2920. A mixture of phthalimide (0.147 g, 1.0 mmol), (R)-(+)-3-chloro-1-phenyl-1-propanol (0.171 g, 1.0 mmol), triphenylphosphine (0.262 g, 1.0 mmol) and diethyl azodicarboxylate (0.174 g, 1.0 mmol) in 5.0 mL of THF was stirred at room temperature for 24 h. The reaction mixture was concentrated in vacuo. The residue was washed with pentane (3×50 mL) and the combined pentane extracts were concentrated and chromatographed (silica, hexanes: EtOAc=8:1 as the eluent) to give the desired product (0.121 g, 50%) as a yellow solid: 1H NMR (400 MHz, CDCl3) δ 7.82 (apparent dd, 2H, J=2.9 Hz), 7.70 (apparent dd, 2H, J=2.9 Hz), 7.56 (m, 2H), 7.39–7.27 (m, 3H), 5.64 (apparent dd, 1H, J=7.0, 9.2 Hz), 3.57 (m, 2H), 3.05 (m, 1H), 2.82 (septet, 1H, J=7.0 Hz); ESMS m/e: 300.1 (M+H)+.

Provenance & Evidence