Methyl iodide → HCID 57680530, compound

Temperature

-78 °C

To a solution of(s)-1-tert-butyl 2-ethyl 4,4-dimethyl-5-oxopyrrolidine-1,2-dicarboxylate (163D) (10 g, 0.035 mol) in dry THF (60 mL) stirred at −78° C. under nitrogen was added a 1 M solution of lithium hexmethyldisilazide in THF (38.5 mL, 0.038 mol). The mixture was stirred at −78° C. for 30 min, iodomethane (5.4 g, 0.038 mol) in THF (5 mL) was added, and the mixture was then stirred 1 h, warmed up to room temperature and continued stirring for additional 3 h. The reaction mixture was quenched with saturated ammonium chloride solution and extracted with CH2Cl2 (3×100 mL). The combined organic layers were dried over Na2SO4, filtered, and evaporated to dryness. The residue was purified by flash chromatography (10-20% EtOAc/hexane) to furnish (163E) (8.2 g, 72%).

1. stirringthe mixture was then stirred 1 h
2. temperaturewarmed up to room temperature
3. stirringcontinued stirring for additional 3 h
4. customThe reaction mixture was quenched with saturated ammonium chloride solution
5. extractionextracted with CH2Cl2 (3×100 mL)
6. dry with materialThe combined organic layers were dried over Na2SO4
7. filtrationfiltered
8. customevaporated to dryness
9. customThe residue was purified by flash chromatography (10-20% EtOAc/hexane)

ORD record

ord-523ccc73e1164db2a5c0fa22ae0384ea

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07879855B2