Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Iodide | HCID 4875 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- | HCID 85083 | — |
| Reactant | 1-(7-Bromo-9,9-difluoro-9H-fluoren-2-yl)-2-chloroethanone | HCID 59611258 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | HCID 59610554 | HCID 59610554 | 88.2% |
Reaction Steps
A mixture of 1-(7-bromo-9,9-difluoro-9H-fluoren-2-yl)-2-chloroethanone (2 g, 5.6 mmol), (S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (1.32 g, 6.1 mmol), potassium carbonate (1.55 g, 11.1 mmol) and potassium iodide (930 mg, 5.6 mmol) in acetone was heated to 60° C. After forty minutes, the reaction was cooled to room temperature and concentrated. The residue was dissolved in a mixture of ethyl acetate and water. The aqueous phase was extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous NH4Cl solution and brine, dried (Na2SO4) and concentrated. The crude material was purified by flash column chromatography to yield (S)-2-(2-(7-bromo-9,9-difluoro-9H-fluoren-2-yl)-2-oxoethyl) 1-tert-butyl pyrrolidine-1,2-dicarboxylate (2.65 g, 88%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09156823B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-787990ca48174aa7aa01d7b32217c3b8 |
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| Source note | uspto-grants-2015_10 |
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