Iodoethane → HCID 86697413, compound

HRID 2276720Notes

Reaction equation

HRID 2276720 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:11]23[CH:16]([CH:17]=[N:18][OH:19])[CH:15]2[CH2:14][N:13]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:12]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]23[CH:16]([CH:17]=[N:18][O:19][CH2:27][CH3:28])[CH:15]2[CH2:14][N:13]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:12]3)[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 86697412HCID 86697412, compound

Product 1

HCID 86697413HCID 86697413, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (23 mg, 0.96 mmol, 60% suspension in mineral oil) in dry DMF (2 mL) at 0° C. under nitrogen atmosphere, was added a solution of tert-butyl 1-(3,4-dichlorophenyl)-6-((hydroxyimino)methyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate (140 mg, 0.38 mmol), obtained in step-1 of example 6, in DMF (2 mL). The reaction mixture was stirred at the same temperature for 30 min followed by the addition of ethyl iodide (0.06 mL, 0.74 mmol). The reaction mixture was stirred at room temperature for 3 h. 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 crude product which was purified by column chromatography (silica gel, 1:9 EtOAc: Pet Ether) to afford pure tert-butyl 1-(3,4-dichlorophenyl)-6-((ethoxyimino)methyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate (75 mg, 50%) as a viscous oil as a mixture of isomers.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 h
  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
  9. customto afford crude product which
  10. customwas purified by column chromatography (silica gel, 1:9 EtOAc: Pet Ether)

Sources & evidence

ORD record
ord-88d43ea55231407a844d68e1e892763d
Source dataset
uspto-grants-2015_09
Patent number
US09133116B2

Reaction notes

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