Hydrochloric Acid → 3-[4-Cyanobenzyl]aminopropanoic acid

Participants

Reaction Steps

4-cyanobenzaldehyde (0.65 g; 5 mmoles) and β-alanine ethyl ester.HCl (0.76 g; 5 mmoles) were dissolved in N,N-dimethylformamide (10 ml) containing 1% acetic acid. After 10 min., sodiumcyanoborohydride (0.35 g; 5 mmoles) was added to the solution. The reaction mixture was stirred at room temperature for 12 hrs. and taken down to dryness under reduced pressure. The residue was treated with 1N lithium hydroxide/methanol (1:1; 20 ml) for 15 min. Methanol was removed and the pH of the remaining solution was adjusted to pH 5 with 50% acetic acid. The product was purified by HPLC using a linear gradient of acetonitrile/water/trifluoroacetic acid. The desired fractions was collected and lyophilized to give 0.81 g of white solid (79% yield). FAB-MS: MH+ =205.1.

Provenance & Evidence