Hexane → Benzyl 2-oxopyrrolidine-1-carboxylate

Reaction equation

[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].CCCCCC.Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]>C1COCC1>[C:14]([N:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6])([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]

Participants

Procedure

To a solution of 2-pyrrolidinone (1.7 g, 21 mmol) in dry THF (25 mL), at −78° C., a 2.5 N solution of n-buthyllithium in n-hexane (8.4 mL, 21 mmol) is added. The mixture is stirred for 30′ and then a solution of benzyl chlorformate (3.03 mL, 21 mmol) in dry THF (30 mL) is added dropwise. The reaction mixture is stirred until the reaction is complete, quenched with saturated aqueous NH4Cl and ectracted with diethyl ether (3×). The combined organic phase is washed with brine and dried over anhydrous Na2SO4. Evaporation of the solvent gives 4 g (87%) of a colourless oil that is used without any further purification.