Benzyl Bromide → 3-Ethyl-3-(3-benzyloxy-phenyl)-azepan-2-one

HRID 1594912Notes

Reaction equation

HRID 1594912 reaction equation
[CH2:1]([C:3]1([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:4]1=[O:10])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C>[CH2:1]([C:3]1([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:4]1=[O:10])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 217062193-Ethyl-3-(3-hydroxy-phenyl)-azepan-2-one

Product 1

HCID 217063013-Ethyl-3-(3-benzyloxy-phenyl)-azepan-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-ethyl-3-(3-hydroxy-phenyl)-azepan-2-one (Example 8, Step B) (1.28 g, 0.0055 mol) in DMF (50 mL) was added Cs2CO3 (1.79 g, 0.055 mmol) and benzyl bromide (0.653 mL, 0.0055 mmol) at ambient temperature. After 1.5 h the reaction was concentrated to remove most of the DMF and the residue was partitioned between EtOAc and H2O. The aqueous layer was washed with EtOAc, the organics combined, washed with brine, and dried (MgSO4). Filtration and concentration to dryness gave the title compound.

Workup

  1. concentrationAfter 1.5 h the reaction was concentrated
  2. customto remove most of the DMF
  3. customthe residue was partitioned between EtOAc and H2O
  4. washThe aqueous layer was washed with EtOAc
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationFiltration and concentration to dryness

Sources & evidence

ORD record
ord-9661498932954ddb9d7d8ff4445cbc5e
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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