Norbornadiene → 1-Methyl-3-{4-[(5R)-2-oxo-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-3-yl]phenyl}-1H-pyrazole-5-carbaldehyde

HRID 456795Notes

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]([C:17]3[CH:21]=[C:20]([CH:22]=[O:23])[N:19]([CH3:24])[N:18]=3)=[CH:13][CH:12]=2)[CH2:6]1)=[N+:2]=[N-:3].[CH:25]12CC(C=C1)C=[CH:26]2>O1CCOCC1>[CH3:24][N:19]1[C:20]([CH:22]=[O:23])=[CH:21][C:17]([C:14]2[CH:15]=[CH:16][C:11]([N:7]3[CH2:6][C@H:5]([CH2:4][N:1]4[CH:26]=[CH:25][N:3]=[N:2]4)[O:9][C:8]3=[O:10])=[CH:12][CH:13]=2)=[N:18]1

Participants

Conditions

Temperature: 90 °C

Procedure

3-{4-[(5R)-5-(Azidomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}-1-methyl-1H-pyrazole-5 carbaldehyde (Intermediate 13, 50 mg, 0.15 mmol), bicyclo[2.2.1]hepta-2,5-diene (0.17 ml, 1.58 mmol) and dioxane (1 ml) were combined and warmed to 90° C. for 4.5 hours. The mixture was evaporated and purified by chromatography on silica gel, eluting with ethyl acetate to give the title compound as a white solid (25 mg).

Workup

customThe mixture was evaporated
custompurified by chromatography on silica gel
washeluting with ethyl acetate

Sources & evidence

ORD record: ord-09160f5e9d4443eaac5617f6e9758e08
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186738B2

Reaction notes

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