Acetic Acid → HCID 86669073, compound

Participants

Reaction Steps

A solution of 1-[2-(2,4,6-trichloro-phenyl)-cyclopropyl]-ethanone O-methyl-oxime (0.19 mmol), prepared as described in example P23, in ethanol (1 ml) and acetic acid (1 ml) was treated at ambient temperature with sodium cyanoborohydride (200 mg, 3.18 mmol) added in one portion. The resulting solution was stirred at ambient temperature for 20 hours. The solvent was evaporated under reduced pressure (co-evaporation with toluene twice) and the residue was slurried with 1 M NaOH (5 ml). The aqueous phase was extracted with ether (3×10 ml), washed with brine and dried over anhydrous Na2SO4. After removal of the solvent, the residue was purified by flash chromatography over silica gel (5 g) (eluent: c-hexane/ethyl acetate 5:1). 25 mg (45.0% of theory) of trans-N-{1-[2-(2,4,6-trichlorophenyl)-cyclopropyl]-ethyl}-O-methyl-hydroxylamine as a mixture of diastereomeres was obtained in form of a clear liquid.

Provenance & Evidence