Acetic Acid → 1-[4,5-Dimethoxy-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]-4-isobutylpiperazine
Reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[C:5]([CH:17]2[CH2:22][C:21]([CH3:24])([CH3:23])[CH2:20][C:19]([CH3:26])([CH3:25])[CH2:18]2)[CH:4]=1.[CH:27](=O)[CH:28]([CH3:30])[CH3:29].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([N:11]2[CH2:12][CH2:13][N:14]([CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:15][CH2:16]2)=[C:5]([CH:17]2[CH2:22][C:21]([CH3:24])([CH3:23])[CH2:20][C:19]([CH3:26])([CH3:25])[CH2:18]2)[CH:4]=1Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of the 1-[4,5-dimethoxy-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine (10 mg, 0.028 mmol) produced in Example (87d) in tetrahydrofuran (1 mL) were added isobutyraldehyde (3.0 mg, 0.042 mmol), sodium triacetoxyborohydride (12 mg, 0.057 mmol) and acetic acid (1.7 mg, 0.028 mmol) in that order, followed by stirring for 60 minutes at room temperature. Saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture, extraction was performed with ethyl acetate, and the organic layer was concentrated. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 1-[4,5-dimethoxy-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]-4-isobutylpiperazine.
Workup
- concentrationthe organic layer was concentrated
- customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)
Sources & evidence
- ORD record
- ord-7b401ecf659749fe9cf485eea61a0c8b
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07425554B2
Reaction notes
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