Methyl iodide → HCID 10774373, compound

HRID 1360159Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCC[CH2:15]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].IC.C(OCC)(=O)C>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH3:15])[C:9]1=[O:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: -78 °C

Procedure

300 mg (1.61 mmol) of 2-oxo-pyrrolidin-1-carboxylic acid t-butyl ester was dissolved in tetrahydrofuran and then cooled to −78° C. To the resulting solution, was dropwise added a solution of 1.7 mL (1.7 mmol) of 1.0 M lithium bis(trimethylsilyl)amide tetrahydrofuran, followed by stirring for 1 hour. 0.19 mL (3.05 mmol) of iodomethane was dropwise added thereto. Thereafter, the temperature was gradually raised to −30° C. for 2 hours. 50 mL of ethyl acetate was added to the solution, and the reaction solution was washed with aqueous ammonium chloride, and an organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, then the residue was purified by column chromatography to give 130 mg (0.65 mmol) of the title compound in a yield of 40%.

Workup

temperatureThereafter, the temperature was gradually raised to −30° C. for 2 hours
washthe reaction solution was washed with aqueous ammonium chloride
dry with materialan organic layer was dried over anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-5594c03475a94808aec87212c60b7d0d
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879848B2

Reaction notes

Loading…