1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 123147808, compound

HRID 2046547Notes

Reaction equation

HRID 2046547 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[CH:6](O)[CH2:7][O:8][C:4]=2[CH:3]=1.C1(P([N:26]=[N+:27]=[N-:28])(C2C=CC=CC=2)=O)C=CC=CC=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[N:26]([CH:6]1[C:5]2[CH:10]=[CH:11][C:2]([Br:1])=[CH:3][C:4]=2[O:8][CH2:7]1)=[N+:27]=[N-:28]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 682967416-Bromo-2,3-dihydro-1-benzofuran-3-ol

Product 1

HCID 123147808HCID 123147808, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In analogy to the procedures described for the preparation of intermediates A-2 [B] and A-2 [C], (rac)-6-bromo-2,3-dihydro-benzofuran-3-ol was treated with diphenylphosphoryl azide, DBU in toluene to give (rac)-3-azido-6-bromo-2,3-dihydro-benzofuran, which was subsequently reduced with triphenylphosphine in THF/water to yield the title compound as light yellow oil. MS: 213 (M+, 1Br).

Sources & evidence

ORD record
ord-30f1c0d7a0774bb3a8c7cab832407ea4
Source dataset
uspto-grants-2013_11
Patent number
US08592426B2

Reaction notes

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