Glutaraldehyde → 9-Azabicyclo[3.3.1]nonan-3-one

HRID 646586Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 646586
[CH2:1]([C:8](O)=O)[C:2]([CH2:4][C:5](O)=[O:6])=O.O.[NH3:12].[CH:13](=O)[CH2:14][CH2:15]CC=O>>[CH:2]12[NH:12][CH:14]([CH2:15][CH2:8][CH2:1]1)[CH2:13][C:5](=[O:6])[CH2:4]2

Komponenten

4

Edukt 3

HCID 3485GlutaraldehydeHCID 68328Acetonedicarboxylic acidHCID 12896473Azane;hydrate

Produkt 1

HCID 1457459-Azabicyclo[3.3.1]nonan-3-one

Versuchsvorschrift

In the first step of the present invention, to an aqueous solution of acetonedicarboxylic acid (3) as a basic material, ammonia water and an aqueous solution of glutaraldehyde (4) are sequentially added slowly under cooling with ice to form a bicyclo-form (5) by condensation reaction. By condensation by Mannich reaction and subsequent decarboxylation, formation of 9-azabicyclo[3.3.1]nonane ring occurs to form 9-azabicyclo[3.3.1]nonan-3-one (5), which can be obtained as a powder only by removing excessive water and ammonia by a freeze-dryer after completion of the reaction.

Aufarbeitung

  1. temperatureunder cooling with ice

Quellen und Nachweise

ORD-Eintrag
ord-7fb61ad4e294428cbdd8aed1e3674d89
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07705152B2

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