HuagongsheHuagongshe Chemistry Print Report · For research reference only
Nitrogen → Tert-butyl 3-fluoro-4-oxopiperidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Selectfluor | HCID 2724933 | — |
| Reactant | tert-Butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate | HCID 10778540 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | Tert-butyl 3-fluoro-4-oxopiperidine-1-carboxylate | HCID 10560711 | — |
Reaction Steps
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of tert-butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate (5.30 g, 19.53 mmol) in dry acetonitrile (25 mL) was added Selectfluor® (8.01 g, 21.48 mmol) at rt. The reaction mixture was stirred at rt for 2 h then poured into EA and successively washed with aq. 1% NaHCO3 and brine. The org. layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by FC (hexanes-EA, 4:1) to afford the title compound as a pale yellow solid. LC-MS-conditions 08: tR=0.55 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09187435B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-ce8b20ad3b254176810e7f065ff098d4 |
| Source note | uspto-grants-2015_11 |