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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 564556Erstellt: 25. Oktober 2026

Sodium hydride → Tert-butyl 4-(3-bromobenzylidene)piperidine-1-carboxylate

https://huagongshe.com/reaction/564556

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktSodium hydrideHCID 24758—
Edukttert-Butyl 4-oxopiperidine-1-carboxylateHCID 735900—
Edukt[(3-Bromophenyl)methyl](triphenyl)phosphanium bromideHCID 19034144—
LösungsmittelDiethyl EtherHCID 3283—
LösungsmittelDimethylformamideHCID 6228—
ProduktTert-butyl 4-(3-bromobenzylidene)piperidine-1-carboxylateHCID 5781340928,6%

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

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08067408B2
Quelldatensatzuspto-grants-2011_11
ORD IDord-961cfee4a57842e1b32e1a502718ea82
Quellennotizuspto-grants-2011_11