Norbornadiene → (5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one

HRID 723806Notes

Reaction equation

HRID 723806 reaction equation
[S:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([CH2:18][N:19]=[N+:20]=[N-:21])[O:15][C:14]3=[O:22])=[CH:9][C:8]=2[F:23])[CH2:3][CH2:2]1.[CH:24]12CC(C=C1)C=[CH:25]2>O1CCOCC1>[S:1]1[CH2:2][CH:3]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([CH2:18][N:19]4[CH:25]=[CH:24][N:21]=[N:20]4)[O:15][C:14]3=[O:22])=[CH:9][C:8]=2[F:23])[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 8473NorbornadieneHCID 11450455(5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-azidomethyloxazolidin-2-one

Product 1

HCID 11302859(5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-oneYield 73.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-azidomethyloxazolidin-2-one (2 g, 5.7 mmol) was dissolved in dioxane (10 ml). Bicyclo[2.2.1]hepta-2,5-diene (3.1 ml, 28.7 mmol) was added and it was refluxed under nitrogen for 18 hours. The solvent was evaporated in vacuo and the residue subjected to chromatography on silica gel eluting with 25% ethylacetate in dichloromethane to give the title compound (1.51 g).

Workup

  1. temperatureit was refluxed under nitrogen for 18 hours
  2. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-502261ae6fe846098c7d5a4f86b798a8
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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