1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 118114292, compound

HRID 2284855Notes

Reaction equation

O[CH:2]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:3]1[CH:19]=[CH:18][C:6]([O:7][CH2:8][C:9]2[O:13][C:12]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C1(P([N:40]=[N+:41]=[N-:42])(C2C=CC=CC=2)=O)C=CC=CC=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[N:40]([CH:2]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:3]1[CH:19]=[CH:18][C:6]([O:7][CH2:8][C:9]2[O:13][C:12]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)=[N+:41]=[N-:42]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of methyl 5-((4-(hydroxy(phenyl)methyl)phenoxy)methyl)-furan-2-carboxylate (325 mg, 0.96 mmol) in toluene (4.5 mL) under nitrogen was added diphenylphosphoryl azide (0.25 mL, 1.15 mmol) followed by DBU (0.17 mL, 1.15 mmol). The reaction was heated at 100° C. for 3 h. The reaction was quenched by the addition of saturated ammonium chloride solution. The aqueous phase was extracted with ethyl acetate (×2). The combined organic phases were washed with brine, dried over MgSO4, filtered and the solvent removed in vacuo. The residue was purified via silica gel chromatography, eluting with 0-25% EtOAc in isohexane, to give the title compound as a colourless oil (293 mg, 84%).

Workup

customThe reaction was quenched by the addition of saturated ammonium chloride solution
extractionThe aqueous phase was extracted with ethyl acetate (×2)
washThe combined organic phases were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
customthe solvent removed in vacuo
customThe residue was purified via silica gel chromatography
washeluting with 0-25% EtOAc in isohexane

Sources & evidence

ORD record: ord-042cef2c124946d4a2f31a2a37d1fafa
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145409B2

Reaction notes

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