Sodium Azide → N-Boc-4-(2-azidoethyl)piperidine

HRID 265857

Reaktionsgleichung

Reaktionsgleichung von HRID 265857
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15]I)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[N-:17]=[N+:18]=[N-:19].[Na+]>CS(C)=O.CCOC(C)=O>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:17]=[N+:18]=[N-:19])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Komponenten

5

Edukt 2

HCID 33557Sodium AzideHCID 9974426Tert-butyl 4-(2-iodoethyl)piperidine-1-carboxylate

Produkt 1

HCID 23282934N-Boc-4-(2-azidoethyl)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 1-4 (27.9 g, 0.082 moles) dissolved in DMSO (400 ml) was added sodium azide (5.61 g, 0.086 moles) at room temperature and the resulting solution was heated at 65° for 2 hrs. The cooled reaction mixture was diluted with 250 ml EtOAc, extracted with 2×100 ml portions of water, 2×50 ml portions of brine and then dried (MgSO4). Solvent removal provided 1-5 as a pale yellow oil, Rf 0.5 (silica gel, 20% acetone/hexane). ##STR13##

Aufarbeitung

  1. temperaturethe resulting solution was heated at 65° for 2 hrs
  2. customThe cooled reaction mixture
  3. extractionextracted with 2×100 ml portions of water, 2×50 ml portions of brine
  4. dry with materialdried (MgSO4)
  5. customSolvent removal

Quellen und Nachweise

ORD-Eintrag
ord-ec27af140ab349c7be387d9655a832c7
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05648368

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