Norborna-diene → HCID 10179280, compound

HRID 723745Notes

Reaction equation

HRID 723745 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:21][C@H:20]([CH2:22][N:23]=[N+:24]=[N-:25])[O:19][C:18]4=[O:26])=[CH:13][C:12]=3[F:27])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[C:28]12CC(CC1)=C[CH:29]=2>O1CCOCC1>[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:21][C@H:20]([CH2:22][N:23]5[CH:29]=[CH:28][N:25]=[N:24]5)[O:19][C:18]4=[O:26])=[CH:13][C:12]=3[F:27])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 18006658Norborna-dieneHCID 86590231HCID 86590231, compound

Product 1

HCID 10179280HCID 10179280, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(5R)-3-(4-(1,4-Dioxa-8-azaspiro[4,5]decan-8-yl)-3-fluorophenyl)-5-azidomethyloxazolidin-2-one (2.44 g, 6.5 mM) was dissolved in dioxane (50 ml), treated with norbornadiene (2.98 g, 32.3 mM) and heated under reflux for 20 hours. After removal of the solvent, the residue was dissolved in dichloromethane (350 ml) washed with water (3×200 ml), and dried over magnesium sulfate. After filtration and evaporation the residue was purified by chromatography on a 20 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 2.5% methanol in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (1.5 g).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 20 hours
  3. customAfter removal of the solvent
  4. dissolutionthe residue was dissolved in dichloromethane (350 ml)
  5. washwashed with water (3×200 ml)
  6. dry with materialdried over magnesium sulfate
  7. filtrationAfter filtration and evaporation the residue
  8. customwas purified by chromatography on a 20 g silica Mega Bond Elut® column
  9. washeluting with
  10. temperaturea gradient increasing in polarity from 0 to 2.5% methanol in dichloromethane
  11. customevaporated

Sources & evidence

ORD record
ord-031cde99fa464637b696fabb7ae17eb3
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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