Sodium cyanoborohydride → HCID 86669069, compound

Participants

Reaction Steps

To a stirred solution of trans 1-[2-(2-chloro-6-fluoro-phenyl)-cyclopropyl]-ethanone O-methyl-oxime (1.1 g; 4.6 mmol) prepared as described in example P21, in acetic acid (10 ml) at ambient temperature was added portionwise sodium cyanoborohydride (0.60 g; 9.3 mmol). The reaction mixture was stirred for 16 hours at ambient temperature then poured in sodium hydrogen carbonate saturated solution (50 ml) and extracted with dichloromethane (3×50 ml). Combined organic layers were dried over anhydrous sodium sulphate. The solvent was removed in vacuo and the residue was purified by flash chromatography over silica gel (elution gradient: cyclohexane/ethyl acetate 99:1 to 1:99) to afford 0.85 g (75% of theory) of trans N-{1-[2-(2-chloro-6-fluoro-phenyl)-cyclopropyl]-ethyl}-O-methyl-hydroxylamine as a mixture of diastereomeres in form of a clear viscous oil.

Provenance & Evidence