Diisopropylamine → HCID 10585948, compound

Participants

Reaction Conditions

Reaction Steps

In an atmosphere of nitrogen and at −78° C., 1.66 N n-butyllithium-hexane solution (7.08 ml) was added dropwise to a tetrahydrofuran (20 ml) solution of diisopropylamine (1.65 ml, 11.75 mmol), and the mixture was stirred at 0° C. for 5 minutes. The reaction solution was cooled to −78° C. and added dropwise to a tetrahydrofuran (20 ml) solution of 4-(S)-fluoromethyl-N-[1-(R)-phenylethyl]-2-pyrrolidone (2.00 g, 9.04 mmol) at −78° C. in an atmosphere of nitrogen. After 15 minutes of stirring at the same temperature, degassing was effected under a reduced pressure, the atmosphere in the reaction container was replaced with oxygen gas and then the reaction mixture was stirred at the same temperature in an atmosphere of oxygen. After completion of the reaction, the reaction solution was mixed with 5% sodium thiosulfate aqueous solution, tetrahydrofuran was evaporated, the thus obtained residue was extracted with ethyl acetate (150 ml×3) and then the resulting organic layers were combined and dried over sodium sulfate. The solvent was evaporated and the thus obtained residue was subjected to a silica gel chromatography to give 1.57 g (73%) of the title compound from the eluate of 3% methanol-chloroform in the form of white crystals.

Provenance & Evidence