Diisopropylamine → HCID 10585948, compound

Temperature

0 °C

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.

1. temperatureThe reaction solution was cooled to −78° C.
2. stirringAfter 15 minutes of stirring at the same temperature
3. customdegassing
4. stirringthe reaction mixture was stirred at the same temperature in an atmosphere of oxygen
5. customAfter completion of the reaction
6. customwas evaporated
7. extractionthe thus obtained residue was extracted with ethyl acetate (150 ml×3)
8. dry with materialdried over sodium sulfate
9. customThe solvent was evaporated

ORD record

ord-b152edc79341407d9c1f1d5b25cd8bff

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06656952B2