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Sodium hydride → tert-Butyl 4-(2-chloro-5-fluoro-4-nitrobenzylidene)piperidine-1-carboxylate

HRID 515301
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 515301
[Cl:1][C:2]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[C:14]([F:20])=[CH:13][C:3]=1[CH2:4]P(=O)(OCC)OCC.O=[C:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1.[H-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[C:14]([F:20])=[CH:13][C:3]=1[CH:4]=[C:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 86670949Diethyl 2-chloro-5-fluoro-4-nitrobenzylphosphonate

Produkt 1

HCID 67194189tert-Butyl 4-(2-chloro-5-fluoro-4-nitrobenzylidene)piperidine-1-carboxylateAusbeute 28,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

Diethyl 2-chloro-5-fluoro-4-nitrobenzylphosphonate (4.06 g, 12.47 mmol) and tert-butyl 4-oxopiperidine-1-carboxylate (2.48 g, 12.47 mmol) were stirred in tetrahydrofuran (47.9 ml) and cooled in an ice bath. Sodium hydride (0.65 g, 16.21 mmol) was added and the reaction taken off the ice bath and stirred for 3.5 hours at room temperature. The reaction was quenched with water and extracted with dichloromethane, dried (magnesium sulphate), filtered and evaporated under reduced pressure. The crude material was purified by silica chromatography using a dichloromethane solvent system. The oil obtained was triturated with heptane and filtered to give the title compound as a yellow solid (1.32 g). 1H NMR (CDCl3, 400 MHz): δ 8.12 (d, 1H), 7.13 (d, 1H), 6.33 (s, 1H), 3.55 (t, 2H), 3.44 (t, 2H), 2.41 (t, 2H), 2.34 (t, 2H), 1.48 (s, 9H)

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. customThe reaction was quenched with water
  3. extractionextracted with dichloromethane
  4. dry with materialdried (magnesium sulphate)
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe crude material was purified by silica chromatography
  8. customThe oil obtained
  9. customwas triturated with heptane
  10. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-6317c51e91b34c5a8beb84b4aad61965
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09108939B2

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