Water → 4-Azido-2-methyl-pyrrolidine-1-carboxylic Acid T-butyl Ester

HRID 1071503Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1071503
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11](OS(C)(=O)=O)[CH2:10][CH:9]1[CH3:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:19]=[N+:20]=[N-:21].[Na+].O.CCCCCC.C(OCC)(=O)C>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([N:19]=[N+:20]=[N-:21])[CH2:10][CH:9]1[CH3:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 33557Sodium AzideHCID 197903964-Methanesulfonyloxy-2-methyl-pyrrolidine-1-carboxylic Acid T-butyl EsterHCID 21226206Ethyl acetate hexane

Produkt 1

HCID 140411954-Azido-2-methyl-pyrrolidine-1-carboxylic Acid T-butyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

The 4-methanesulfonyloxy-2-methyl-pyrrolidine-1-carboxylic acid t-butyl ester (135.21 mg, 0.48 mmol) was taken up in dry DMF under argon and sodium azide (156.00 mg, 2.40 mmol) was added. The reaction was then heated to 60° C. for 48 h. The reaction was poured into water and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with sat NaHCO3 and brine then dried over MgSO4. The solution was filtered and the solvent removed under reduced pressure. The product was isolated by flash chromatography. (5:1 hexane-ethyl acetate) Yield 93.41 mg.

Aufarbeitung

  1. extractionthe aqueous layer was extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with sat NaHCO3 and brine
  3. dry with materialthen dried over MgSO4
  4. filtrationThe solution was filtered
  5. customthe solvent removed under reduced pressure
  6. customThe product was isolated by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f5b78fb38d1c45b3b62efda05b70320a
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06906067B2

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