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

Participants

Reaction Conditions

Reaction Steps

To a cold (10° C.) stirred solution of 2-fluoro-5-methoxybenzyl bromide (35, 50 mg, 0.23 mmol), t-butylglycinate Schiff base 3 (68 mg, 0.23 mmol) and potassium iodide (4.2 mg, 0.05 mmol) in dioxane (2.0 mL) was added dropwise over 30–45 min. benzyltrimethylammonium hydroxide (0.069 mL, 0.23 mmol, 40% aqueous). The reaction mixture was then brought to room temperature and stirred for an additional 3 h. After cooling to 0° C., water (2.0 mL) was added and the mixture was extracted with toluene (6×10 mL). The organic extracts were washed with water (20 mL) and dried over sodium sulfate. Evaporation of the solvent afforded a colorless oil, which was not purified (33%) and the alkylated product 40 was not obtained.

Provenance & Evidence