Tert-Butyl nitrite → tert-Butyl 4-azido-3-iodobenzylcarbamate

HRID 1961487Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1961487
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][C:3]=1[I:17].N(OC(C)(C)C)=O.[Si]([N:29]=[N+:30]=[N-])(C)(C)C>CC#N>[N:1]([C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][C:3]=1[I:17])=[N+:29]=[N-:30]

Komponenten

5

Edukt 3

HCID 10906Tert-Butyl nitriteHCID 78378AzidotrimethylsilaneHCID 10383091tert-Butyl 4-amino-3-iodobenzylcarbamate

Produkt 1

HCID 86661980tert-Butyl 4-azido-3-iodobenzylcarbamateAusbeute 87,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

tert-Butyl 4-amino-3-iodobenzylcarbamate (1.0 g, 2.87 mmol) was dissolved in CH3CN (6.0 ml). The solution was cooled to 0° C., tert-butyl nitrite (444.3 mg, 4.30 mmol) and TMS azide (397.1 mg, 3.45 mmol) were added. The mixture was then stirred at r.t for 2.0 h. The solvents were removed under vacuum and the residue purified by flash chromatography (Pet. Ether/EtOAc 85:15) affording 936 mg (87%) of the title compound.

Aufarbeitung

  1. customThe solvents were removed under vacuum
  2. customthe residue purified by flash chromatography (Pet. Ether/EtOAc 85:15)

Quellen und Nachweise

ORD-Eintrag
ord-f1d7edcee4fb4b16bc6067874f8b8fdd
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415333B2

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