Hydrochloric Acid → Tert-butyl 2-(cyclopentylamino)acetate

Participants

Reaction Steps

Cyclopentyl amine (50.0 g, 587 mmols) was dissolved in anhydrous ether (500 ml) and triethylamine (69.3 g, 685 mols) was added. The resulting solution was cooled in an ice bath and then tert-butyl bromoacetate (95.4 g, 489 mmols) in ether (150 ml) was added slowly over approximately three hours. The reaction mixture was allowed to stir overnight at room temperature. The reaction was acidified to pH 1 with aqueous hydrochloric acid and the layers were separated. The aqueous layer was washed with ethyl acetate and then basified to pH 10 with aqueous ammonium hydroxide. The product was extracted several times into methylene chloride and the combined organic extract was washed twice with water, once with brine, dried over magnesium sulfate, filtered, and evaporated to yield the desired product as a slightly yellow oil (56.9 g, 58.4%).

Provenance & Evidence