Sodium Azide → (R)-2-azidomethyl-morpholine-4-carboxylic acid tert-butyl ester

HRID 1043231Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1043231
S(O[CH2:12][C@@H:13]1[O:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]1)(C1C=CC(C)=CC=1)(=O)=O.[N-:26]=[N+:27]=[N-:28].[Na+]>CN(C)C=O>[N:26]([CH2:12][C@@H:13]1[O:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]1)=[N+:27]=[N-:28]

Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 54043639(R)-tert-butyl 2-(tosyloxymethyl)morpholine-4-carboxylate

Produkt 1

HCID 57686784(R)-2-azidomethyl-morpholine-4-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of EXAMPLE 442A (1.66 g, 4.47 mmol) and sodium azide (0.581 g, 8.94 mmol) in anhydrous N,N-dimethylformamide (10 mL) was stirred at 90° C. for 4 hours. The mixture was cooled and concentrated to dryness. The residue was taken up in 5% aqueous sodium carbonate solution and extracted with methylene chloride. The combined organic layers was dried (MgSO4), filtered and concentrated to provide the title compound.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated to dryness
  3. extractionextracted with methylene chloride
  4. dry with materialThe combined organic layers was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-50a371da2b68492eb552a1fcac81f389
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557983B2

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