Ammonia → HCID 12192619, compound

Participants

Reaction Steps

L-Phenylalanine methyl ester hydrochloride (7) (8 g, 37.09 mmol) was added in portions, during 15 minutes, to a solution of methylmagnesium iodide [prepared from methyl iodide (13.76 ml, 222.6 mmol)] in diethyl ether (304 ml) and refluxed for 6 hours. To promote hydrolysis, a saturated solution of ammonium chloride (19.38 g, 370.9 mmol) in water (70 ml) was added dropwise with vigorous stirring. The insoluble product was filtered off through celite, and the organic layer was separated and dried with sodium sulphate. Concentration in vacuo gave a colourless oil. The aqueous layer was made alkaline by addition of aqueous ammonia. The product was extracted with diethyl ether, dried with sodium sulphate and concentrated in vacuo. The oily residues were then combined and distilled giving the title compound (8) (2.686 g, 41%).

Provenance & Evidence