[CH3:1][O:2][N:3]=[C:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:16])[CH3:5].C([BH3-])#N.[Na+]>C(O)(=O)C.C(=O)([O-])O.[Na+]>[Cl:16][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([F:15])[C:9]=1[C@@H:7]1[CH2:8][C@H:6]1[CH:4]([NH:3][O:2][CH3:1])[CH3:5]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.
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