Norbornadiene → (5R)-3-(5-Bromopyrid-2-yl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one

HRID 747202Notes

Reaction equation

HRID 747202 reaction equation
[N:1]([CH2:4][C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][N:12]=2)[CH2:6]1)=[N+:2]=[N-:3].[CH:18]12CC(C=C1)C=[CH:19]2>O1CCOCC1>[Br:17][C:14]1[CH:15]=[CH:16][C:11]([N:7]2[CH2:6][C@H:5]([CH2:4][N:1]3[CH:19]=[CH:18][N:3]=[N:2]3)[O:9][C:8]2=[O:10])=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 8473NorbornadieneHCID 15341129(5R)-5-(Azidomethyl)-3-(5-bromopyrid-2-yl)-1,3-oxazolidin-2-one

Product 1

HCID 59749446(5R)-3-(5-Bromopyrid-2-yl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-oneYield 71.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(5R)-5-(Azidomethyl)-3-(5-bromopyrid-2-yl)-1,3-oxazolidin-2-one (5.60 g, 18.7 mM) was dissolved in 1,4-dioxane (12 ml). Bicyclo[2.2.1]hepta-2,5-diene (10.3 g, 112 mM) was added and the yellow solution was stirred at 100° for 16 hours. The brown solution was concentrated and the residue was purified by flash chromatography eluting with ethyl acetate. Relevant fractions were combined to give the desired product (4.36 g) as a beige solid.

Workup

  1. concentrationThe brown solution was concentrated
  2. customthe residue was purified by flash chromatography
  3. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-a4c6397bc2cb4761969bcc423e5e0a1d
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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