Triphenylphosphine → HCID 53923612, compound

Participants

Reaction Conditions

Reaction Steps

Diethyl azodicarboxylate (0.45 mL, 2.7 mmol) is added dropwise to a solution of triphenyl phosphine (0.71 g, 2.7 mmol) in THF (18 mL) at -78° C. After 15 minutes a solution of (±)-(2R*, 3R*)-2-Hydroxymethyl-3-(4-methoxybenzenesulfonyl)-7-phenylheptanoic acid (1 g, 2.5 mmol) in THF (8 mL) is added dropwise over 5 minutes. After 30 minutes the bath is removed and the reaction is allowed to warm to 23° C. and stir for 45 minutes. The reaction is concentrated in vacuo and the crude reaction mixture is purified by column chromatography (silica, CH2Cl2) to yield pure (±)-3-(R*)-[1-(R*)-(4-methoxybenzenesulfonyl)-5-phenypentyl]oxetan-2-one (0.63 g, 63%): 1H NMR (300 MHz, CDCl3) δ 7.75-7.70 (m, 2H), 7.28-7.23 (m, 2H), 7.19-7.14 (m, 1H), 7.12-7.09 (m, 2H), 7.03-6.95 (m, 2H), 4.41 (t, J=6.2 Hz, 1H), 4.31 (t, J=5.4 Hz, 1H), 4.03-3.95 (m, 1H), 3.87 (s, 3H), 3.44-3.37 (m, 1H), 2.53 (t, J=7.2 Hz, 2H), 1.89-1.81 (m, 2H), 1.58-1.38 (m, 4H); 13C NMR (75.5 MHz, CDCl3) δ 167.83, 164.25, 141.89, 130.91, 128.21, 128.17, 125.65, 114.65, 113.91, 65.04, 63.83, 55.68, 50.47, 35.16, 30.91, 27.04, 25.73; MS (FAB) m/e 389 (M+H)+.

Provenance & Evidence