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 86655157 | HCID 86655157 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86655156 | HCID 86655156 | 150.8% |
Reaction Steps
To (1R)-1-methyl-2-oxo-2-tetrahydro-1-H-1-pyrrolylethyl 2-bromohexanoate (4.8 g, 15 mmol), NaI (2.3 g, 15 mmol), triethylamine (2.4 g, 24 mmol) and tetrahydrofuran (5 mL) were added. To the solution, p-methoxyaniline (2.4 g, 20 mmol) and tetrahydrofuran (5 mL) were added. The mixture was stirred at 37° C. for 1 hour and then at 20° C. for 5 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 then the solvent was removed away in reduced pressure in order to obtain 8.2 g of oil. The conversion ratio to the obtained compound was 1000, and the diastereo ratio calculated by NMR analysis was 94.5:5.5.
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-5e6636dc6ad3478894fa3a2aa03b98ea |
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| Source note | uspto-grants-2013_02 |
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