Acrolein → 3-(1-Nitrocyclopentyl)propionaldehyde

HRID 2226411

Reaktionsgleichung

Reaktionsgleichung von HRID 2226411
[N+:1]([CH:4]1[CH2:8][CH2:7][CH2:6][CH2:5]1)([O-:3])=[O:2].[CH:9]([CH:11]=[CH2:12])=[O:10].[H-].[Na+]>O1CCCC1>[N+:1]([C:4]1([CH2:12][CH2:11][CH:9]=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5]1)([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 7847AcroleinHCID 24758Sodium hydrideHCID 75714Nitrocyclopentane

Produkt 1

HCID 136797083-(1-Nitrocyclopentyl)propionaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Condense nitrocyclopentane (prepared from bromocyclopentane and sodium nitrite) and acrolein in tetrahydrofuran in the presence of sodium hydride to obtain 3-(1-nitrocyclopentyl)propionaldehyde. Treat this aldehyde with p-toluenesulfonic acid in methanol and isolate 3-(1-nitrocylopentyl) propionaldehyde dimethyl acetal. Hydrogenate this compound with Raney nickel. Isolate 3-(1-aminocyclopentyl)propionaldehyde dimethylacetal and dissolve in aqueous acetone in the presence of p-toluenesulfonic acid and heat under reflux, followed by addition of toluene and azeotrope the mixture to give 1-azaspiro[4.4]-Δ1 -nonane.

Quellen und Nachweise

ORD-Eintrag
ord-42e9d4709faa4cc0b06ce629b74c733f
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05348944

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