HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 517972Generated: October 27, 2026
Triphenylphosphine → tert-Butyl 4-(2-(5-bromo-3-(trifluoromethyl)pyridin-2-yloxy)ethyl)piperidine-1-carboxylate
https://huagongshe.com/reaction/517972
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diisopropyl diazene-1,2-dicarboxylate | HCID 75555 | — |
| Reactant | 1-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine | HCID 854140 | — |
| Reactant | HCID 178517592 | HCID 178517592 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | tert-Butyl 4-(2-(5-bromo-3-(trifluoromethyl)pyridin-2-yloxy)ethyl)piperidine-1-carboxylate | HCID 69931589 | 69.6% |
Reaction Steps
To a suspension of 5-bromo-2-hydroxy-3-(trifluoromethyl)pyridine (6.90 g) in 1,4-dioxane (100 ml), triphenylphosphine (9.44 g) and tert-butyl 4-(2-hydroxyethyl)-piperidine-1-carboxylate (7.41 g) were added. Then diisopropyl azodicarboxylate (DIAD, 7.52 ml, 7.67 g) was added dropwise and stirred at 20° C. for 18 h. Solvent was then removed under reduced pressure and residue purified by Biotage SNAP cartridge KP-Sil column (340 g, hepane:ethyl acetate=1:0, 5:1 to 4:1) to give 9.0 g orange oil as tert-butyl 4-(2-(5-bromo-3-(trifluoromethyl)pyridin-2-yloxy)ethyl)-piperidine-1-carboxylate (70%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09115126B2 |
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| Source dataset | uspto-grants-2015_08 |
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| ORD ID | ord-0c33095b22c44370b44da9dd3585948a |
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| Source note | uspto-grants-2015_08 |
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