[CH3:1][C:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][C:4](=O)[CH:3]=1.C([O-])(=O)C.[Na+].S(O)(O)(=O)=O.[NH2:21]O.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(O)C.O>[CH3:1][C:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][CH:4]([NH2:21])[CH:3]=1An ethanol-water solution (1:3, 4 mL) of 3,4,4-trimethylcyclohex-2-enone (500 mg, 3.62 mmol) and sodium acetate (356 mg, 4.35 mmol) was stirred with hydroxylamine sulfate (475 mg, 2.89 mmol) at 70° C. for 40 hours. After completion of the reaction, the reaction solution was extracted with ethyl acetate, and the resulting organic layer was evaporated under reduced pressure. The resulting residue was dissolved in tetrahydrofuran (5 mL), mixed with lithium aluminum hydride (412 mg, 10.9 mmol) at 0° C. and stirred at room temperature for 2 hours. After completion of the reaction, the reaction solution was mixed with saturated aqueous sodium sulfate, dried over anhydrous magnesium sulfate and filtered through celite, and the solvent was removed by vacuum distillation to give the desired product.
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