Sodium Iodide → tert-Butyl 3-(azidomethyl)piperidine-1-carboxylate

HRID 1478589Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1478589
S(O[CH2:12][CH:13]1[CH2:18][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+].[Na+].[I-]>CN(C=O)C>[N:26]([CH2:12][CH:13]1[CH2:18][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

5

Edukt 3

HCID 5238Sodium IodideHCID 33557Sodium AzideHCID 18369320Tert-butyl 3-((P-tolylsulfonyloxy)methyl)piperidine-1-carboxylate

Produkt 1

HCID 22647380tert-Butyl 3-(azidomethyl)piperidine-1-carboxylateAusbeute 93,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

tert-butyl 3-((tosyloxy)methyl)piperidine-1-carboxylate (8.85 g, 24 mmol) was dissolved in DMF (100 ml), and then NaN3 (6.24 g, 96 mmol) and NaI (0.36 g, 2.40 mmol) were added, followed by stirring at 70° C. for hours. After the completion of the reaction, the reaction mixture was extracted with H2O, EA, and brine, followed by drying (Na2SO4), filtration, and concentration under reduced pressure, and the residue was purified by column chromatography (EA:Hex=1:10), to give tert-butyl 3-(azidomethyl)piperidine-1-carboxylate (5.38 g, 92%).

Aufarbeitung

  1. customAfter the completion of the reaction
  2. extractionthe reaction mixture was extracted with H2O, EA, and brine
  3. customby drying
  4. filtration(Na2SO4), filtration, and concentration under reduced pressure
  5. customthe residue was purified by column chromatography (EA:Hex=1:10)

Quellen und Nachweise

ORD-Eintrag
ord-cd12c09ff1d5406b9f302d2ee11c55ec
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403831B2

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