Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (Diethylamino)sulfur trifluoride | HCID 123472 | — |
| Reactant | HCID 19935801 | HCID 19935801 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 68519937 | HCID 68519937 | 33.8% |
Reaction Steps
To a cooled (0° C.) solution of 1-benzyl-3-(3,5-difluorophenyl)pyrrolidin-3-ol (1.9 g, 6.6 mmol) in dichloromethane (20 mL) was added dropwise diethylaminosulphurtrifluoride (1.05 mL, 7.26 mmol) dissolved in dichloromethane (5 mL) and the mixture was stirred at ambient temperature for 1 h. Additional diethylaminosulphurtrifluoride (0.1 mL, 0.69 mmol) was added and stirring was continued 0.5 h. Aqueous sodium carbonate (10%, 50 mL) was added and the phases separated. The aqueous phase was extracted with dichloromethane (50 mL) and the pooled organic phase was dried (MgSO4) and evaporated. Purification by flash column chromatography gave the title compound (0.65 g). MS m/z (rel. intensity, 70 eV) 291 (M+, 44), 200 (17), 133 (51), 132 (45), 91 (bp).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08188301B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-05998c6f2f8c4281b1d3ebc45e4358c9 |
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| Source note | uspto-grants-2012_05 |
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