Lithium azide → tert-Butyl 3-azidopiperidine-1-carboxylate

HRID 1584266Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1584266
[N-:1]=[N+:2]=[N-:3].[Li+].CS(O[CH:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]1)(=O)=O>CN(C=O)C>[N:1]([CH:14]1[CH2:15][CH2:10][CH2:11][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]1)=[N+:2]=[N-:3]

Komponenten

4

Edukt 2

HCID 88163Lithium azideHCID 568122N-Boc-3-mesyloxypiperidine

Produkt 1

HCID 547722tert-Butyl 3-azidopiperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Lithium azide (1.35 g, 27.6 mmol) was added to a solution of 3-methanesulfonyloxy-N-t-butoxycarbonylpiperidine (1.54 g, 5.51 mmol) in DMF (20 ml) and the resulting mixture heated at 60° C. for 48 h. Removal of the solvent in vacuo and chromatographic purification (3:1 hexane/ethyl acetate) of the residue afforded the title compound. 1H NMR (CDCl3) d 1.46 (s, 9 H), 1.75 (m, 2 H), 1.96 (m, 2 H), 3.13 (br s, 1 H), 3.46 (m, 2 H), 3.57 (m, 2 H).

Aufarbeitung

  1. customRemoval of the solvent
  2. customin vacuo and chromatographic purification (3:1 hexane/ethyl acetate) of the residue

Quellen und Nachweise

ORD-Eintrag
ord-69a1ccff9fbb4bc38743eb41e68b56db
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05932606

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