Hydrochloric Acid → Ethyl 2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of 51.5 g. 4-trimethylsilyloxypyrrolidin-2-one in 500 ml. anhydrous acetonitrile are added 133 ml. ethyl bromoacetate. The solution is heated to 50° C. and 26.7 g. of 80% sodium hydride (dispersion in mineral oil) are slowly added in small amounts. When the addition is completed, the reaction mixture is heated under reflux for 30 minutes and then cooled to ambient temperature. To the reaction mixture obtained containing ethyl 2-(4-trimethylsilyloxypyrrolidin-2-on-1-yl)-acetate (b.p. 160° C./3 mm.Hg) are added 50 ml. 1 N hydrochloric acid. The reaction mixture is stirred for 30 minutes and then evaporated to dryness. The residue obtained is chromatographed on a silica gel column, using ethyl acetate as the elution agent, 45 g. ethyl 2-(4-hydroxypyrrolidin-2-on-1-yl)-acetate being obtained; b.p. 180° C./0.8 mm.Hg; Rf 0.17 (silica gel; eluant ethyl acetate).

Provenance & Evidence