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

HRID 1790602

Reaktionsgleichung

Reaktionsgleichung von HRID 1790602
C[CH:2]1[CH2:9][CH:8]2[CH:6]([O:7]2)[CH2:5][N:4]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)(=[O:12])=[O:11])[CH2:3]1.[N-:19]=[N+:20]=[N-:21].[Na+].[NH4+].[Cl-].[CH3:25]O>O>[N:19]([CH:8]1[CH:9]([CH3:25])[CH2:2][CH2:3][N:4]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)(=[O:11])=[O:12])[CH2:5][CH:6]1[OH:7])=[N+:20]=[N-:21]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 220366865-Methyl-3-(pyridine-2-sulfonyl)-8-oxa-3-aza-bicyclo[5.1.0]octane

Produkt 1

HCID 220366394-Azido-5-methyl-1-(pyridine-2-sulfonyl)-azepan-3-olAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. temperatureThe resulting mixture was refluxed overnight
  2. customAfter the removal of MeOH
  3. additionthe residue was diluted in EtOAc
  4. washwashed with 10% NaHCO3 and brine
  5. customPurified on column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7aa9cdfe43284d549adfbad416cbc22d
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07071184B2

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