Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | P-Anisidine | HCID 7732 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sodium Sulfite | HCID 24437 | — |
| Reactant | HCID 58339724 | HCID 58339724 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86655160 | HCID 86655160 | 57.6% |
Reaction Steps
To (1S)-1-methyl-2-oxo-2-tetrahydro-1-H-1-pyrrolylethyl 2-bromo-3-cyclopropylpropanoate (418 mg, 1.3 mmol), NaI (198 mg, 1.3 mmol), triethylamine (214 g, 2.1 mmol) and tetrahydrofuran (5 mL) were added. To the solution, p-methoxyaniline (211 mg, 1.7 mmol) and tetrahydrofuran (3 mL) were added. The mixture was stirred at room temperature for 24 hours and further at 40° C. for 20 hours. To the mixture, a saturated sodium sulfite aqueous solution and ethyl acetate were added for extraction. The obtained extract was dried with anhydrous magnesium sulfate, and the solvent was removed away under reduced pressure. The residue was purified with silica gel chromatography to obtain 270 mg of the target compound (yield: 57%, The diastereo ratio calculated by NMR analysis was 92:8.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08383833B2 |
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| Source dataset | uspto-grants-2013_02 |
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| ORD ID | ord-d1d229d964ef4fa29c60f9e6b0bff0b3 |
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| Source note | uspto-grants-2013_02 |
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