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Borane (0.412 ml of a 1M solution in tetrahydrofuran) was added to a stirred solution of (±)-3-[2,4-bis(methoxymethoxy)phenyl]cyclohexanone oxime (85 mg) in tetrahydrofuran (2 ml) at 0° C. under argon. After 2 hr, acetic acid (1 ml) was added and the mixture was allowed to warm to ambient temperature. After 16 hr, sodium hydrogen carbonate (20 ml of a saturated aqueous solution) was added, the mixture was extracted with ethyl acetate (3×20 ml) and the combined organic extracts were dried over magnesium sulfate and evaporated in vacuo. The crude residue was purified by flash column chromatography (SiO2, dichloromethane/methanol, 9:1 v/v) to furnish two compounds as clear gums which were identified as diastereoisomers of the title compound; trans-isomer (12 mg, 14%) m/z (ES+) 312 (M+H)+; cis-isomer (0.017 g, 20%) m/z (ES+) 312 (M+H)+.

1. waitAfter 16 hr
2. extractionthe mixture was extracted with ethyl acetate (3×20 ml)
3. dry with materialthe combined organic extracts were dried over magnesium sulfate
4. customevaporated in vacuo
5. customThe crude residue was purified by flash column chromatography (SiO2, dichloromethane/methanol, 9:1 v/v)
6. customto furnish two compounds as clear gums which