Norbornadiene → (R)-5-((1H-1,2,3-Triazol-1-yl)methyl)-3-(3-fluoro-4-iodophenyl)oxazolidin-2-one

HRID 459010Notes

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])=[C:13]([F:18])[CH:12]=2)[CH2:6]1)=[N+:2]=[N-:3].[CH:19]12CC(C=C1)C=[CH:20]2>O1CCOCC1>[F:18][C:13]1[CH:12]=[C:11]([N:7]2[CH2:6][C@H:5]([CH2:4][N:1]3[CH:20]=[CH:19][N:3]=[N:2]3)[O:9][C:8]2=[O:10])[CH:16]=[CH:15][C:14]=1[I:17]

Participants

Conditions

Temperature: 100 °C

Procedure

(5R)-5-(Azidomethyl)-3-(3-fluoro-4-iodophenyl)-1,3-oxazolidin-2-one (Intermediate 5, 30.3 g, 72.9 mmol) was stirred in 1,4-dioxane. Bicyclo[2.2.1]hepta-2,5-diene (40.3 g, 437 mmol) was added and the reaction was heated at 100° C. overnight. The resulting brown mixture was filtered and the desired product was obtained as a light brown solid (14.8 g).

Workup

filtrationThe resulting brown mixture was filtered

Sources & evidence

ORD record: ord-85c6d8966a3844879e39fea16bee7d85
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192974B2

Reaction notes

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