Norbornadiene → HCID 21876611, compound

HRID 723813Notes

Reaction equation

HRID 723813 reaction equation
[S:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:12]([F:13])=[CH:11][C:10]([N:14]3[CH2:18][C@H:17]([CH2:19]OS(C)(=O)=O)[O:16][C:15]3=[O:25])=[CH:9][C:8]=2[F:26])[CH2:3][CH2:2]1.[N-:27]=[N+:28]=[N-:29].[Na+].[N-]=[N+]=[N-].[CH:34]12CC(C=C1)C=[CH:35]2>CN(C)C=O.C(OC(=O)C)C.O1CCOCC1>[S:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:12]([F:13])=[CH:11][C:10]([N:14]3[CH2:18][CH:17]([CH2:19][N:27]4[CH:35]=[CH:34][N:29]=[N:28]4)[O:16][C:15]3=[O:25])=[CH:9][C:8]=2[F:26])[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 8473NorbornadieneHCID 33557Sodium AzideHCID 33558AzideHCID 10179421HCID 10179421, compound

Product 1

HCID 21876611HCID 21876611, compoundYield 30.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

Methanesulfonic acid (5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-2-oxo-oxazolidin-5-ylmethyl ester (1.1 g, 5.7 mmol) was dissolved in dry N,N-dimethylformamide (5 ml) and sodium azide (0.35 g, 5.43 mmol) was added. It was heated at 60° C. for 18 hours. The reaction mixture was cooled to room temperature, diluted with ethylacetate, washed with water and dried over magnesium sulfate. Solvent was removed under vacuum to give an oil. The crude intermediate azide was not characterized. It was taken up in 1,4-dioxane (20 ml), bicyclo[2.2.1]hepta-2,5-diene (1.0 g, 10.9 mmol) was added and it was refluxed for 12 hours. Solvent was removed under vacuum and the residue chromatographed on silica gel with 5% methanol in dichloromethane to give the title compound (0.62 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customSolvent was removed under vacuum
  5. customto give an oil
  6. temperatureit was refluxed for 12 hours
  7. customSolvent was removed under vacuum
  8. customthe residue chromatographed on silica gel with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-90010021a8334bcfb82d4096c32d1210
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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