Acetic Acid → 3-Ethylproline hydrochloride

Participants

Reaction Steps

Diethyl 1-Acetyl-3-ethylpyrrolidine-2,2-dicarboxylate (373 g, 0.95 mol) was suspended in 6N HCl (2 L) and HOAc (500 mL) and heated at reflux for 20 h. The reaction mixture was cooled, washed with EtOAc (1L), then concentrated in vacuo to give an oil which crystallized upon trituration with ether to give the title compound. 1H NMR (D2O) δ 4.23 (d, 1H, J=8 Hz), 3.84 (d, 1H, J=8 Hz), 3.15-3.4 (m, 4H), 2.33-2.44 (m, 1H), 2.19-2.4 (m, 1H), 2.02-2.15 (m, 2H), 1.53-1.72 (m, 3H), 1.23-1.43 (m, 2H), 1.0-1.15 (m, 1H), 0.75-0.83 (m, 6H).

Provenance & Evidence