Allyl iodide → HCID 54332185, compound

Participants

Reaction Steps

Benzyloxycarbonyl-L-alanine t-butyl ester (10.0 g, 35.8 mmol) was dissolved in dry THF. Allyl iodide (7.4 mL, 78.8 mmol) was added followed by sodium hydride (1.80 g, 45.0 mmol). The reaction was left stirring at room temperature overnight. The reaction was evaporated and taken up in ethyl acetate. It was extracted with water and treated with sodium metabisulfite. The ethyl acetate was extracted with 1N aqueous sodium carbonate, dried over anhydrous magnesium sulfate, filtered and evaporated under vacuum. The crude product was flash chromatographed (silica gel, hexane followed by hexane:ethyl acetate 95:5) to give N-benzyloxycarbonyl, N-allyl-L-alanine t-butyl ester (6.8 g, 60%). 1H NMR (CDCl3) δ7.33 (s, 5H), 6.17-5.67 (m, 1H), 5.20 (d, 4H), 1.75-1.70 (s/d, 12H).

Provenance & Evidence