Acetic Acid → (+/-)-n-{3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexyl}hydroxylamine
Reaction equation
B.[CH3:2][O:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][O:14][CH3:15])[CH:9]=[CH:8][C:7]=1[CH:16]1[CH2:21][CH2:20][CH2:19][C:18](=[N:22][OH:23])[CH2:17]1.C(O)(=O)C.C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:2][O:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][O:14][CH3:15])[CH:9]=[CH:8][C:7]=1[CH:16]1[CH2:21][CH2:20][CH2:19][CH:18]([NH:22][OH:23])[CH2:17]1Participants
Procedure
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)+.
Workup
- waitAfter 16 hr
- extractionthe mixture was extracted with ethyl acetate (3×20 ml)
- dry with materialthe combined organic extracts were dried over magnesium sulfate
- customevaporated in vacuo
- customThe crude residue was purified by flash column chromatography (SiO2, dichloromethane/methanol, 9:1 v/v)
- customto furnish two compounds as clear gums which
Sources & evidence
- ORD record
- ord-d19d6a26bf0945c7ada3d93a6b755d0a
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06933319B2
Reaction notes
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