Methyl iodide → 3-Ethyl-1-(2-methoxy-ethyl)-3-(3-benzyloxy-phenyl)-azepan-2-one

HRID 1594916Notes

Reaction equation

HRID 1594916 reaction equation
[H-].[Na+].[CH2:3]([C:5]1([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:17]=2)[CH2:11][CH2:10][CH2:9][CH2:8][N:7]([CH2:12][CH2:13][OH:14])[C:6]1=[O:15])[CH3:4].[CH3:30]I>CN(C=O)C>[CH2:3]([C:5]1([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:17]=2)[CH2:11][CH2:10][CH2:9][CH2:8][N:7]([CH2:12][CH2:13][O:14][CH3:30])[C:6]1=[O:15])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 217062773-Ethyl-1-(2-hydroxy-ethyl)-3-(3-benzyloxyphenyl)-azepan-2-one

Product 1

HCID 217062903-Ethyl-1-(2-methoxy-ethyl)-3-(3-benzyloxy-phenyl)-azepan-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.017 g, 0.425 mmol) was added to a solution of 3-ethyl-1-(2-hydroxy-ethyl)-3-(3-benzyloxyphenyl)-azepan-2-one, as described in Example 54, Step C, (0.12 g, 0.327 mmol) in DMF (5 mL) at 0° C. with stirring. After 20 min CH3I (0.041 mL, 0.653 mmol) was added and stirring was continued at room temperature for 16 h. The reaction was quenched with H2O and the solvents removed in vacuo. The residue was partitioned between EtOAc and saturated NaHCO3 solution. The organic layer was separated, washed with brine and dried (MgSO4). Filtration and concentration gave the title compound.

Workup

  1. stirringstirring
  2. customThe reaction was quenched with H2O
  3. customthe solvents removed in vacuo
  4. customThe residue was partitioned between EtOAc and saturated NaHCO3 solution
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-66d4ad5bb07e4ff38eca47ec2507830d
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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