1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 118139438, compound

HRID 2046540Notes

Reaction equation

HRID 2046540 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6](O)[CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1.BrC1C=C2C(C(=O)CCO2)=CC=1.[BH4-].[Na+].C1(P([N:41]=[N+:42]=[N-:43])(C2C=CC=CC=2)=O)C=CC=CC=1.C1CCN2C(=NCCC2)CC1>C(O)C.C1(C)C=CC=CC=1>[N:41]([CH:6]1[C:5]2[C:10](=[CH:11][C:2]([Br:1])=[CH:3][CH:4]=2)[O:9][CH2:8][CH2:7]1)=[N+:42]=[N-:43]

Participants

8

Reactant 5

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 4311764Sodium borohydrideHCID 223357367-bromo-3,4-dihydro-2H-1-benzopyran-4-oneHCID 68296695HCID 68296695, compound

Product 1

HCID 118139438HCID 118139438, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

In analogy to the procedures described fort he preparation of intermediates A-2 [B] and A-2 [C], (rac)-7-bromo-chroman-4-ol prepared from 7-bromo-chroman-4-one with sodium borohydride in ethanol at 60-70° C., was treated with diphenylphosphoryl azide, DBU in toluene to give (rac)-4-azido-7-bromo-chroman, which was subsequently reduced with triphenylphosphine in THF/water to yield the title compound as light yellow oil. MS: 227 (M+, 1Br).

Sources & evidence

ORD record
ord-89d225724fa44ec8b11300e3c60f572d
Source dataset
uspto-grants-2013_11
Patent number
US08592426B2

Reaction notes

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