Bromoacetonitrile → 3-Cyano-2-piperidin-1-yl-propionic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

Treat a −78° C. solution of ethyl 1-piperidine acetate (20.0 g, 0.117 mol) in THF (200 mL) with a 2M solution of lithium diisopropylamide in heptane/THF/ethylbenzene (70.1 mL, 0.140 mol) and stir at −78° C. for 20 minutes under N2. Treat the reaction with bromoacetonitrile (21.00 g, 0.175 mol) and stir at −78° C. for 15 minutes. Warm the reaction to room temperature and stir 4 hours. Quench the reaction into saturated ammonium chloride. Dilute the reaction with ethyl acetate and wash with water. Dry the organic layer (Na2SO4), remove the solvent in vacuo to afford crude product, and purify with a 0 to 20% ethyl acetate in hexanes gradient to afford 6.74 g (27%) of the titled product. Rf=0.41 (3/1 hexanes/ethyl acetate). ES MS (m/z): 211 (M+1).

Provenance & Evidence