2-Butene, 1-bromo-3-methyl- → 3-[2-(S)-(4-chloro-benzyl)-5-methyl-hex-4-enoyl]-4-(R)-methy-5-(S)-phenyl-oxazolidin-2-one

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Reaction Conditions

Reaction Steps

To a cooled (−78° C.) solution of 3-[3-(4-chloro-phenyl)-propionyl]-4-(R)-methyl-5-(S)-phenyl-oxazolidin-2-one, 32, (500 mg, 1.46 mmol) in THF (15 mL) is added sodium bis(trimethylsilyl)-amide (1.75 mL, 1.0M solution in THF, 1.75 mmol). The resulting solution is stirred at −78° C. then 4-bromo-2-methyl-2-butene (0.20 mL, 1.75 mmol) is slowly added. The resulting solution is stirred at room temperature overnight, and the solvent removed under reduced pressure. The crude product is purified by preparative HPLC to afford 213 mg (36% yield) of the desired compound as a colorless oil. 1H NMR (CDCl3 300 MHz) δ 0.83 (d, J=6.6 Hz, 3H), 1.62 (s, 3H), 1.70 (s, 3H), 2.20–2.55 (m, 2H), 2.77–3.10 (m, 2H), 4.20–4.35 (m, 1H), 4.55–4.68 (m, 1H), 5.15–5.25 (m, 1H), 5.38 (d, J=7.2 Hz, 1H), 7.15–7.45 (m, 9H). MS (ESI) m/z 412 (M+H+)

Provenance & Evidence