Norborna-diene → HCID 69365298, compound

HRID 723782Notes

Reaction equation

HRID 723782 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][C@H:14]([CH2:16][N:17]=[N+:18]=[N-:19])[O:13][C:12]2=[O:20])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:21]12CC(CC1)=C[CH:22]=2>O1CCOCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:15][C@H:14]([CH2:16][N:17]3[CH:22]=[CH:21][N:19]=[N:18]3)[O:13][C:12]2=[O:20])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 18006658Norborna-dieneHCID 86590238HCID 86590238, compound

Product 1

HCID 69365298HCID 69365298, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(5R)-3-(4-t-Butylphenyl)-5-azidomethyloxazolidin-2-one (400 mg, 1.46 mM) was dissolved in dioxane (8 ml), treated with norbornadiene (1.3 g, 14.1 mM) and heated under reflux for 6 hours. After removal of the solvent, the residue was dissolved ethyl acetate, and purified by flash chromatography on silica, eluting with the same solvent. Relevant fractions were combined to give the desired product (260 mg, mp 140–142°). MS (EI): 300 (M+) for C16H20N4O2

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6 hours
  3. customAfter removal of the solvent
  4. dissolutionthe residue was dissolved ethyl acetate
  5. custompurified by flash chromatography on silica
  6. washeluting with the same solvent

Sources & evidence

ORD record
ord-ea0b422c0a5641619c3732d51f223088
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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