Methyl iodide → HCID 15524176, compound

Temperature

0 °C

The following reaction was carried out under a nitrogen atmosphere. At -78° C., n-butyl lithium (5.39 ml, 1.68 N, n-hexane solution, 9.06 mmol) was added dropwise to a tetrahydrofuran solution (40 ml) of diisopropylethylamine (1.37 ml, 9.75 mmol), and the mixture was warmed to 0° C. and stirred for 30 minutes. At -78° C., to this was further added dropwise a tetrahydrofuran solution (20 ml) of (4S)-4-(1-ethoxycarbonylcyclopropyl)-1-[(S)-1-phenylethyl]-2-pyrrolidone (2.10 g, 6.97 mmol). After an additional 15 minutes of stirring, methyl iodide (2.17 ml, 34.8 mmol) was added dropwise thereto, and the mixture was stirred for 30 minutes while warming to 0° C. After completing the reaction, this was cooled in an ice bath and mixed with a saturated ammonium chloride aqueous solution (150 ml) and then tetrahydrofuran was evaporated. The resulting residue was extracted with chloroform (150 ml×3), and the organic layer was dried over anhydrous sodium sulfate. After evaporating the solvent, the resulting residue was purified by a silica gel column chromatography (silica gel, 160 ml; ethyl acetate:hexane=2:3), to thereby obtain 1.90 g (87%) of the title compound.

1. customThe following reaction
2. stirringAfter an additional 15 minutes of stirring
3. stirringthe mixture was stirred for 30 minutes
4. temperaturewhile warming to 0° C
5. customthe reaction
6. temperaturethis was cooled in an ice bath
7. customtetrahydrofuran was evaporated
8. extractionThe resulting residue was extracted with chloroform (150 ml×3)
9. dry with materialthe organic layer was dried over anhydrous sodium sulfate
10. customAfter evaporating the solvent
11. customthe resulting residue was purified by a silica gel column chromatography (silica gel, 160 ml; ethyl acetate:hexane=2:3)

ORD record

ord-f0bc59eb0a514e7a9d358cb2376a986b

Source dataset

uspto-grants-2000_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06121285