Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hexane | HCID 8058 | — |
| Reactant | 2,2-Difluoro-2-(fluorosulfonyl)acetic acid | HCID 2737516 | — |
| Reactant | Benzyl 3-(hydroxymethyl)piperidine-1-carboxylate | HCID 2776577 | — |
| Reactant | Ammonia methanol | HCID 21705897 | — |
| Catalyst | Copper iodide | HCID 83717 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 58495810 | HCID 58495810 | 61% |
Reaction Steps
Benzyl 3-(hydroxymethyl)piperidine-1-carboxylate (2.49 g, 10.0 mmol) was dissolved in acetonitrile (100 mL), to which copper iodide (I) (2.86 g, 15.0 mmol) and 2,2-difluoro-2-(fluorosulfonyl)acetic acid (2.66 g, 15.0 mmol) were added, followed by stirring at 80° C. for 20 minutes. The mixture was brought down to room temperature, to which adequate amounts of hexane and ethyl acetate were added, followed by neutralization with a 2M ammonia/methanol solution. Impurities were filtered off, and the solvent was distilled off under reduced pressure. The residue thus obtained was purified by basic silica gel column chromatography (hexane:ethyl acetate, 100:0-0:100, V/V) to give the desired title compound (1.82 g, yield 61%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08685981B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-b2bf19e2c4fb446281673320570400d1 |
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| Source note | uspto-grants-2014_04 |
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