Sodium cyanoborohydride → O-methyl-N-[1-(2,2,4-trimethyl-cyclohex-3-enyl)-ethyl]-hydroxylamine

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반응 단계

To a stirred solution of 1-(2,2,4-trimethyl-cyclohex-3-enyl)-ethanone O-methyl-oxime (0.27 g; 1.40 mmol) in acetic acid (3 mL) was added portionwise sodium cyanoborohydride (0.20 g; 3.00 mmol). The reaction mixture was stirred at 24° C. for 16 hours under nitrogen atmosphere. Most of acetic acid was removed under reduced pressure. The yellow sticky oil obtained was dissolved in dichloromethane and poured in 1M sodium hydroxide which was extracted with dichloromethane. Combined organic layers were washed with sodium bicarbonate and dried over sodium sulfate. The solvent was removed in vacuo to afford 0.26 g of colorless oil which was subject to flash-master column chromatography (Elution gradient: cyclohexane/ethyl acetate 99:1 to 80:20) to afford 88 mg (33% of theory) of diastereomer A as a clear oil and 58 mg (22% of theory) of diastereomer B as a clear oil.

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