(2S,5S,E)-2-benzyl-1,6-bis((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-methylhex-3-ene-1,6-dione → (2R,5S)-2-benzyl-1,6-bis((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-methylhexane-1,6-dione

Participants

Reaction Steps

To a solution of (2S,5S,E)-2-benzyl-1,6-bis((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-methylhex-3-ene-1,6-dione (250 mg, 0.440 mmol) in EtOAc (5 mL) was added 10% Pd/C (73 mg, 0.069 mmol). The reaction mixture was purged with nitrogen and stirred under an atmosphere of hydrogen (balloon) overnight. The reaction mixture was filtered through CELITE® and concentrated to afford (2R,5S)-2-benzyl-1,6-bis((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-methylhexane-1,6-dione (223 mg, 0.392 mmol, 89% yield) which was used without further purification. Anal. Calcd. for C34H36N2O6 m/z 568.3. found: 569.0 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.33-7.29 (m, 4H), 7.24-7.21 (m, 8H), 7.04-7.02 (m, 3H), 4.64-4.62 (m, 2H), 4.19-4.11 (m, 4H), 4.04 (m, 1H), 3.66 (bs, 1H), 3.32 (m, 1H), 3.01-2.9 (m, 2H), 2.78 (m, 1H), 2.61 (m, 1H), 2.40 (m, 1H), 1.71-1.62 (m, 4H), 0.91 (t, J=7.4 Hz, 3H).

Provenance & Evidence