Sodium cyanoborohydride → HCID 86669075, compound

Participants

Reaction Steps

To a stirred solution of trans 1-[2-(2,4,5-trichloro-thiophen-3-yl)cyclopropyl]-ethanone O-methyl-oxime (2.85 g; 9.5 mmol) prepared as described in example P24, in acetic acid (20 ml) at ambient temperature was added portionwise sodium cyanoborohydride (1.80 g; 29 mmol). The reaction mixture was stirred for 50 hours at ambient temperature then poured on sodium hydroxide solution (0.5M; 150 ml) and extracted with dichloromethane (3×50 ml). Combined organic layers were washed with sodium hydroxide solution (0.5M; 100 ml) and 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 80:20) to afford 1.78 g (62% of theory) of trans O-methyl-N-{1-[2-(2,4,5-trichloro-thiophen-3-yl)-cyclopropyl]-ethyl}-hydroxylamine as a mixture of diastereomeres in form of a yellow oil.

Provenance & Evidence