Norborna-diene → HCID 69365832, compound

HRID 723781Notes

Reaction equation

HRID 723781 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]=[N+:16]=[N-:17])[O:11][C:10]2=[O:18])=[CH:5][CH:4]=1.[C:19]12CC(CC1)=C[CH:20]=2>O1CCOCC1>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]3[CH:20]=[CH:19][N:17]=[N:16]3)[O:11][C:10]2=[O:18])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 18006658Norborna-dieneHCID 91613900HCID 91613900, compound

Product 1

HCID 69365832HCID 69365832, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(5R)-3-(4-Methylthiophenyl)-5-azidomethyloxazolidin-2-one (1.62 g, 6.14 mM) was dissolved in dioxane (30 ml), treated with norbornadiene (2.98 g, 31.5 mM) and heated under reflux for 6 hours. After removal of the solvent, the residue was dissolved in the minimum of hot ethyl acetate, filtered, cooled, then diluted with isohexane to precipitate the desired product (600 mg).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6 hours
  3. customAfter removal of the solvent
  4. dissolutionthe residue was dissolved in the minimum of hot ethyl acetate
  5. filtrationfiltered
  6. temperaturecooled
  7. additiondiluted with isohexane
  8. customto precipitate the desired product (600 mg)

Sources & evidence

ORD record
ord-fe0bffb147204490837e7626037995d5
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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