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Norbornadiene → (5R)-3-(4-Iodophenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one

HRID 747206
Notes
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Reaction equation

HRID 747206 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]([I:17])=[CH:13][CH:12]=2)[CH2:6]1)=[N+:2]=[N-:3].[CH:18]12CC(C=C1)C=[CH:19]2>O1CCOCC1>[I: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])=[CH:12][CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 8473NorbornadieneHCID 59749482(5R)-5-(azidomethyl)-3-(4-iodophenyl)-1,3-oxazolidin-2-one

Product 1

HCID 59749410(5R)-3-(4-Iodophenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-oneYield 66.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

(5R)-5-(Azidomethyl)-3-(4-iodophenyl)-1,3-oxazolidin-2-one (10.0 g, 29.1 mmol) was dissolved in 1,4-dioxane (100 ml). Bicyclo[2.2.1]hepta-2,5-diene (9.4 ml, 87.2 mmol) was added and the mixture heated to 100° C. for 24 h. The solution was cooled and purified by silica flash chromatography with 1-10% methanol in dichloromethane as eluent giving 7.2 g of the desired product.

Workup

  1. temperatureThe solution was cooled
  2. custompurified by silica flash chromatography with 1-10% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-d5d171c3a97c4168abce45490510844c
Source dataset
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07396847B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes