Ethyl Acetate → Benzyl 3-amino-3-(2-ethoxy-2-oxoethyl)pyrrolidine-1-carboxylate

Participants

Reaction Steps

A solution of benzyl 3-oxopyrrolidine-1-carboxylate (2.03 g, 10 mmol) and ammonium acetate (977 mg, 12.7 mmol) in EtOH (10 mL) was treated with ethyl malonate (1.07 mL, 9.09 mmol). The resulting solution was heated to reflux for 4 h and cooled to room temperature. Ethyl acetate (200 mL) was added and the solution was washed with saturated NaHCO3 (25 mL), brine (25 mL), dried over MgSO4 and concentrated to dryness. The mixture was filtered through a silica gel plug with ethyl acetate followed by methanol to elute the title compound as a yellow oil (600 mg, 19%). 1H NMR (400 MHz, CD3OD) δ 7.40-7.32 (m, 5H), 4.23 (q, 2H, J=7.4 Hz), 3.81-3.76 (m, 1H), 3.66-3.56 (m, 3H), 2.94 (s, 2H), 2.29-2.24 (m, 2H), 1.29 (t, 3H, J=7.4 Hz). MS ESI 307.1 [M+H]+, calcd for [C16H22N2O4+H]+ 307.16.

Provenance & Evidence