Cyanoacetic acid → HCID 59385358, compound

Participants

Reaction Steps

A solution of 2.52 g (30 mmol) of cyanoacetic acid in 80 mL of dry THF was stirred at −78° C. as 24.6 mL (49.2 mmol) of 2.0 M i-PrMgCl in THF was added. After 1 h, a solution of 3.00 g (10 mmol) 1-tert-butoxycarbonyl-4-phenylpiperidine-4-carboxylic acid (Maybridge, cat. no. JFD 01929) and 1.93 g (12 mmol) of 1,1′-carbonyldiimidazole in 20 mL of THF was added. The reaction mixture was allowed to warm to rt. After 16 h, the mixture was poured into 300 mL of water and the pH lowered to 4 with conc. AcOH. The mixture was then extracted with EtOAc, dried over MgSO4 and concentrated. Purification on silica gel using 1:1 EtOAc-hexanes as eluant afforded 4-(2-cyanoacetyl)-4-phenylpiperidine-1-carboxylic acid tert-butyl ester.

Provenance & Evidence