HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Sodium hydride → Tert-butyl 4-(3-bromobenzylidene)piperidine-1-carboxylate
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Sodium hydride | HCID 24758 | — |
| Edukt | tert-Butyl 4-oxopiperidine-1-carboxylate | HCID 735900 | — |
| Edukt | [(3-Bromophenyl)methyl](triphenyl)phosphanium bromide | HCID 19034144 | — |
| Lösungsmittel | Diethyl Ether | HCID 3283 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | Tert-butyl 4-(3-bromobenzylidene)piperidine-1-carboxylate | HCID 57813409 | 28,6% |
Reaktionsschritte
To [(3-bromophenyl)methyl](triphenyl)phosphonium bromide (1.13 mg, 2.2 mmol) in DMF (4 mL) was added NaH (52.8 mg, 2.2 mmol) after which the mixture was stirred at RT for 5 min before 1,1-dimethylethyl 4-oxo-1-piperidinecarboxylate (400 mg, 2.0 mmol) was added. This mixture was stirred at RT for 1 h. The resultant mixture was diluted with Et2O (25 mL), washed with H2O (12+2×8 mL), brine (8 mL), dried over NaSO4, and filtered. The filtrate was concentrated and purified with CombiFlash chromatograph to afford the title compound (0.2014 g, 28%). LC-MS m/z 352 (M+H)+.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08067408B2 |
| Quelldatensatz | uspto-grants-2011_11 |
| ORD ID | ord-961cfee4a57842e1b32e1a502718ea82 |
| Quellennotiz | uspto-grants-2011_11 |