Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4,4-Difluoropiperidine hydrochloride | HCID 2758351 | — |
| Reactant | (S)-1-Phenylethyl 2-bromo-2-phenylacetate | HCID 59166394 | — |
| Catalyst | Tetrabutylammonium Iodide | HCID 67553 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59540381 | HCID 59540381 | 92.4% |
Reaction Steps
To a solution of the product from Example 138A (1.00 g, 3.13 mmol) in tetrahydrofuran (20 mL) at room temperature was added triethylamine (1.75 mL, 12.5 mmol) and tetrabutylammonium iodide (0.46 g, 1.25 mmol). The mixture was stirred for 5 minutes and then 4,4-difluoropiperidine hydrochloride (0.74 g, 4.70 mmol) was added as the free base in THF. The mixture was stirred for 1 hour at room temperature and then heated to 55° C. overnight. The cooled mixture was washed with brine, concentrated, then purified by column chromatography (EtOAc-hexane) to provide the title compound (1.04 g, 92% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09278922B2 |
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| Source dataset | uspto-grants-2016_03 |
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| ORD ID | ord-3b43cd5895394a27a705b7731ed47867 |
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| Source note | uspto-grants-2016_03 |
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