Potassium Iodide → Tert-butyl 3-iodoazetidine-1-carboxylate

HRID 47887Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 47887
CS(O[CH:6]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]1)(=O)=O.[I-:17].[K+]>CN(C)C=O>[I:17][CH:6]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]1

Komponenten

4

Edukt 2

HCID 4875Potassium IodideHCID 10753243Tert-butyl 3-(methanesulfonyloxy)azetidine-1-carboxylate

Produkt 1

HCID 11000522Tert-butyl 3-iodoazetidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of tert-butyl 3-[(methylsulfonyl)oxy]-1-azetidinecarboxylate (prepared as described in Synlett 1998, 379; 5.0 g, 19.9 mmol), and potassium iodide (16.5 g, 99.4 mmol) in N,N-dimethylformamide (25 mL), was heated at 100° C. for 42 h. The cooled mixture was partitioned between water and ethyl acetate, and the layers separated. The organic phase was dried over MgSO4, concentrated under reduced pressure and the residue azeotroped with xylene. The crude product was purified by flash column chromatography (dichloromethane as eluant) to give the title compound, 3.26 g.

Aufarbeitung

  1. customThe cooled mixture was partitioned between water and ethyl acetate
  2. customthe layers separated
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customthe residue azeotroped with xylene
  6. customThe crude product was purified by flash column chromatography (dichloromethane as eluant)

Quellen und Nachweise

ORD-Eintrag
ord-c5438f609dd440dca37921365ee7c575
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699991B2

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