Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 1-Pyrrolidinecarboxylic acid, 2-oxo-, 1,1-dimethylethyl ester | HCID 379000 | — |
| Reactant | LiHMDS tetrahydrofuran | HCID 23714775 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 10774373 | HCID 10774373 | 40.4% |
Reaction Steps
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%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07879848B2 |
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| Source dataset | uspto-grants-2011_02 |
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| ORD ID | ord-5594c03475a94808aec87212c60b7d0d |
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| Source note | uspto-grants-2011_02 |
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