Formaldehyde → 1-Methyl-3-hydroxyazetidine-3-carboxylic acid

HRID 2049995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2049995
Cl.[OH:2][C:3]1([C:7]([OH:9])=[O:8])[CH2:6][NH:5][CH2:4]1.[CH2:10]=O>O.O.[Pt]=O>[CH3:10][N:5]1[CH2:6][C:3]([OH:2])([C:7]([OH:9])=[O:8])[CH2:4]1

Komponenten

5

Edukt 2

HCID 712FormaldehydeHCID 670516543-Hydroxyazetidine-3-carboxylic acid hydrochloride

Produkt 1

HCID 203431201-Methyl-3-hydroxyazetidine-3-carboxylic acidAusbeute 74,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 86587499Platinum oxide monohydrateKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 500 mg (3.26 mmoles) of 3-hydroxyazetidine-3-carboxylic acid hydrochloride in 15 ml of water are added 1.06 ml of 37% formalin and 250 mg of platinum oxide monohydrate, and the mixture is kept at ambient temperature under atmospheric pressure for 46 hours. The catalyst is filtered off and washed with water. The combined filtrate and washings are evaporated under reduced pressure. The residue (0.79 g) is dissolved in 10 ml of water, adsorbed on 30 ml of Amberlite IR-120 B (H+), and eluted with 100 ml of 2 N aqueous ammonium hydroxide solution. The eluate is evaporated under reduced pressure. The residue (431 mg) is crystallized from water-acetone to yield 1-methyl-3-hydroxyazetidine-3-carboxylic acid as prisms.

Aufarbeitung

  1. filtrationThe catalyst is filtered off
  2. washwashed with water
  3. customThe combined filtrate and washings are evaporated under reduced pressure
  4. dissolutionThe residue (0.79 g) is dissolved in 10 ml of water
  5. washeluted with 100 ml of 2 N aqueous ammonium hydroxide solution
  6. customThe eluate is evaporated under reduced pressure
  7. customThe residue (431 mg) is crystallized from water-acetone

Quellen und Nachweise

ORD-Eintrag
ord-6429c318e65548dd8dbde497d5b46bbe
Quelldatensatz
uspto-grants-1980_04
Patentnummer
US04199570

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