Iodoethane → HCID 86697403, compound

HRID 2276713Notes

Reaction equation

HRID 2276713 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:11](=[N:25][OH:26])[CH:12]2[CH:17]3[CH:13]2[CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16]3)[CH:7]=[CH:8][C:9]=1[Cl:10].[CH2:27](I)[CH3:28]>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([C:11](=[N:25][O:26][CH2:27][CH3:28])[CH:12]2[CH:17]3[CH:13]2[CH2:14][N:15]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:16]3)[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 86697404HCID 86697404, compound

Product 1

HCID 86697403HCID 86697403, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (35 mg, 0.87 mmol, 60% suspension in mineral oil) in dry DMF (3 mL) at 0° C. under nitrogen atmosphere, was added a solution of tert-butyl 6-((3,4-dichlorophenyl)(hydroxyimino)methyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate (200 mg, 0.54 mmol), obtained in step-1 of example 1, in DMF (3 mL) The reaction mixture was stirred at the same temperature for 30 min followed by the addition of ethyl iodide (0.09 mL, 1.1 mmol). The reaction mixture was stirred at room temperature overnight. After completion of the reaction as confirmed by TLC, the reaction mixture was quenched by saturated solution of ammonium chloride and the crude compound was extracted with ethyl acetate. The organic layer was washed with water, separated, dried over anhydrous sodium sulphate and concentrated in vacuo to afford tert-butyl 6-((3,4-dichlorophenyl)(ethoxyimino)methyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate (150 mg, 70%) as a viscous oil which was used without any purification for the next step.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. customAfter completion of the reaction
  3. customthe reaction mixture was quenched by saturated solution of ammonium chloride
  4. extractionthe crude compound was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. customseparated
  7. dry with materialdried over anhydrous sodium sulphate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fff4828d141f496e86ee66186df8a14c
Source dataset
uspto-grants-2015_09
Patent number
US09133116B2

Reaction notes

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