HCID 68938085, compound → HCID 68942419, compound

HRID 532438Notes

Reaction equation

HRID 532438 reaction equation
C(S(C)(=O)=O)=C.[CH3:7][S:8]([CH2:11][CH2:12][N:13]1[CH:18]2[CH2:19][CH2:20][CH:14]1[CH2:15][CH:16]([O:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=1)[CH2:17]2)(=[O:10])=[O:9].[N+](C1C=CC(OC2CC3NC(CC3)C2)=CC=1)([O-])=O>CO>[CH3:7][S:8]([CH2:11][CH2:12][N:13]1[CH:14]2[CH2:20][CH2:19][CH:18]1[CH2:17][CH:16]([O:21][C:22]1[CH:23]=[CH:24][C:25]([NH2:28])=[CH:26][CH:27]=1)[CH2:15]2)(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 68938085HCID 68938085, compoundHCID 68941134HCID 68941134, compound

Product 1

HCID 68942419HCID 68942419, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

8-(2-Methanesulfonylethyl)-3-(4-nitrophenoxy)-8-azabicyclo[3.2.1]octane Methyl vinyl sulfone (585.9 mg) was added to a solution of 3-(4-nitrophenoxy)-8-azabicyclo[3.2.1]octane (1.0 g) in methanol (3.7 ml) and heated at 60° C. for 12 h. The solvent was then removed in vacuo and the residue was taken up in ethyl acetate. The ethyl acetate phase was washed with water and dried over sodium sulfate, and the solvent was removed in vacuo. The crude product was purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol 9:1). The product with the molecular weight of 354.42 (C16H22N2O5S) was obtained in this way; MS (ESI): 355 (M+H+).

Workup

  1. customThe solvent was then removed in vacuo
  2. washThe ethyl acetate phase was washed with water
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed in vacuo
  5. customThe crude product was purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol 9:1)
  6. customThe product with the molecular weight of 354.42 (C16H22N2O5S) was obtained in this way

Sources & evidence

ORD record
ord-7729177ab3834c6bbf06ca4818f73a92
Source dataset
uspto-grants-2014_10
Patent number
US08853208B2

Reaction notes

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