Iodoethane → HCID 86697413, compound

Participants

Reaction Steps

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.

Provenance & Evidence