Réaction #53318

Équation de réaction

glycine ethyl ester hydrochloride

bromoacetaldehyde diethyl acetal

cesium carbonate

sodium iodide

hydrochloric acid

→

title compound

ethyl 2-[(2,2-diethoxyethyl)amino]acetate

Solvants

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   Lavagewashed with ethyl acetate
2. 2
   Extractionextracted with methylene chloride
3. 3
   SéchageThe organic layer was dried over anhydrous sodium sulfate
4. 4
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure

Mode opératoire

To a suspension of the glycine ethyl ester hydrochloride (1.00 g) and bromoacetaldehyde diethyl acetal (1.08 ml) in N,N-dimethylformamide (30 ml), were added cesium carbonate (4.67 g) and sodium iodide (107 mg) and the mixture was stirred at 100° C. for 4 hours. The reaction mixture was adjusted to pH 2 with 1N hydrochloric acid and washed with ethyl acetate. The aqueous layer was adjusted to pH 11 with 1N aqueous solution of sodium hydroxide and extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and thereafter the solvent was distilled off under reduced pressure to obtain the title compound (860 mg).

Source