Reaktion #1877784

Reaktionsgleichung

5-methyl-3-(pyridine-2-sulfonyl)-8-oxa-3-aza-bicyclo[5.1.0]octane

MeOH

NaN3

NH4Cl

→

title compound

Ausbeute 64.0%

4-Azido-5-methyl-1-(pyridine-2-sulfonyl)-azepan-3-ol

Ausbeute 64.0%

Lösungsmittel

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting mixture was refluxed overnight
2. 2
   SonstigeAfter the removal of MeOH
3. 3
   workup.ADDITIONthe residue was diluted in EtOAc
4. 4
   Waschenwashed with 10% NaHCO3 and brine
5. 5
   SonstigePurified on column chromatography

Vorschrift

5-methyl-3-(pyridine-2-sulfonyl)-8-oxa-3-aza-bicyclo[5.1.0]octane (230 mg, 0.86 mmol) was dissolved in the mixture of 8 ml MeOH and 2 ml H2O. NaN3 (170 mg, 2.6 mmol) and NH4Cl (140 mg, 2.6 mmol) were added to the solution. The resulting mixture was refluxed overnight. After the removal of MeOH, the residue was diluted in EtOAc and washed with 10% NaHCO3 and brine. Purified on column chromatography gave the title compound (170 mg, yield 64%). MS (M+H+) 312.2; 1H-NMR (400 Hz, CDCl3): d=8.69(d, 1H), 8.04–7.94(m, 2H), 7.54 (m, 1H) 4.00–2.95 (m, 7H), 2.20(m, 1H), 1.90–1.74(m, 2H), 0.98(d, 3H).

Quelle