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

HRID 1790602

Reaction equation

HRID 1790602 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-7aa9cdfe43284d549adfbad416cbc22d
Source dataset
uspto-grants-2006_07
Patent number
US07071184B2

Linked notes

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