Hydrochloric Acid → 3-Hydroxyazetidine-3-carboxylic acid hydrochloride

HRID 2049994Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2049994
C([N:14]1[CH2:17][C:16]([OH:21])([C:18]([OH:20])=[O:19])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.[ClH:22]>O1CCOCC1.[Pd]>[ClH:22].[OH:21][C:16]1([C:18]([OH:20])=[O:19])[CH2:17][NH:14][CH2:15]1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 203431191-Benzhydryl-3-hydroxy-azetidine-3-carboxylic acid

Produkt 1

HCID 670516543-Hydroxyazetidine-3-carboxylic acid hydrochlorideAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 2.383 g (8.4 mmoles) of crude 1-benzhydryl-3-hydroxyazetidine-3-carboxylic acid in 64 ml of 50% aqueous dioxane is added 2.1 ml of concentrated hydrochloric acid, and the mixture is catalytically hydrogenated for 32 hours in the presence of 924 mg of 10% palladium-charcoal under hydrogen pressure of 5 kg/cm2. The catalyst is filtered off and washed with an aqueous dioxane. The combined filtrate and washings are evaporated under reduced pressure during which the precipitating oily material is removed by washing with ether. The residue is washed with acetone and recrystallized from dimethylformamide-acetone to yield 1.051 g of 3-hydroxyazetidine-3-carboxylic acid hydrochloride as prisms in 82% yield.

Aufarbeitung

  1. filtrationThe catalyst is filtered off
  2. washwashed with an aqueous dioxane
  3. customThe combined filtrate and washings are evaporated under reduced pressure during which the precipitating oily material
  4. customis removed
  5. washby washing with ether
  6. washThe residue is washed with acetone
  7. customrecrystallized from dimethylformamide-acetone

Quellen und Nachweise

ORD-Eintrag
ord-ca64bcd6113649a4bfedbb6278bf4805
Quelldatensatz
uspto-grants-1980_04
Patentnummer
US04199570

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