Malonic Acid → 3-Amino-3-cyclopropylpropanoic acid

HRID 2377095Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2377095
[CH:1]1([CH:4]=O)[CH2:3][CH2:2]1.[C:6]([O-:9])(=[O:8])[CH3:7].[NH4+:10].C(O)(=O)CC(O)=O>C(O)C>[NH2:10][CH:4]([CH:1]1[CH2:2][CH2:3]1)[CH2:7][C:6]([OH:9])=[O:8]

Komponenten

5

Edukt 3

HCID 867Malonic AcidHCID 123114CyclopropanecarboxaldehydeHCID 517165Ammonium Acetate

Produkt 1

HCID 101540633-Amino-3-cyclopropylpropanoic acidAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of cyclopropanecarboxaldehyde (150.2 g, 2.1 mol), ammonium acetate (329.9 g, 4.3 mol), malonic acid (223 g, 2.1 mol), and ethanol (850 mL) was stirred at reflux for 19 h. The reaction was analyzed by LCMS and determined to be complete. The mixture was allowed to cool to room temperature. The heterogeneous mixture was further cooled with an ice-bath and stirred 3 h prior to collecting the solid precipitate by suction filtration. The cake was washed with cold ethanol (displacement wash: 250 mL) and the solids dried under vacuum to provide 146.5 g of the desired compound (53% yield) as a white solid. mp: 206-208° C.

Aufarbeitung

  1. temperatureat reflux for 19 h
  2. temperatureThe heterogeneous mixture was further cooled with an ice-bath
  3. stirringstirred 3 h
  4. customto collecting the solid precipitate
  5. filtrationby suction filtration
  6. washThe cake was washed with cold ethanol (displacement wash: 250 mL)
  7. customthe solids dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f2ef3fd474ef44aa82b1e977994a12a9
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07468375B2

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