Sodium Iodide → 2-(Benzhydrylidene-amino)-3-(2-fluoro-5-methoxy-phenyl)-propionic acid tert-butyl ester

Participants

Reaction Steps

LHMDS (92 mg, 0.55 mmol) was added to a solution of t-butylglycinate Schiff base 3 (136 mg, 0.46 mmol) in THF (1.5 mL) A mixture containing 2-fluoro-5-methoxy-benzyl bromide (35, 100 mg, 0.46 mmol) and sodium iodide (138 mg, 0.92 mmol) in THF (2.0 mL) was immediately added to the resulting enolate solution at −78° C. The combined mixture was warmed to room temperature, stirred for 2 h, diluted with 1:1 ether/pentane (25 mL), washed with brine (3×15 mL), dried (sodium sulfate) and concentrated to afford 40 as a crude yellow oil (108%). Once examined, the pure product was made in 97% yield (193 mg).

Provenance & Evidence