Hydrochloric Acid → HCID 73424848, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of acetonitrile (1.5 mL, 29 mmol) in THF (60 mL) was added n-butyl lithium (2.5 M solution in hexane, 10.8 mL, 29 mmol) at −78° C. The solution was stirred at about −78° C. for about 10 min and a solution of 1-tert-butyl 2-methyl (2S)-pyrrolidine-1,2-dicarboxylate (5.64 g, 25 mmol, US2007197506) in 15 mL of THF was added. The mixture was stirred at about −78° C. for about 1 hr and was subsequently allowed to reach rt (overnight). Water was added and the mixture acidified to pH 3 with 1N aqueous hydrochloric acid. The layers were separated and the organic layer was washed with water (10 mL) and brine (10 mL), dried (MgSO4), filtered and concentrated in vacuo to give tert-butyl (2S)-2-(2-cyanoacetyl)pyrrolidine-1-carboxylate (5.8 g, 24.3 mmol, 97%) as a yellow oil.

Provenance & Evidence