Sodium Hydroxide → 1-[1-(3-Tert-butoxy-2-pyrazinylmethyl)piperidin-4-yl]-2-[2-(trifluoromethyl)phenyl]ethanone
Reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8](=[O:20])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])[CH2:4][CH2:3]1.[C:21]([O:25][C:26]1[C:27]([CH:32]=O)=[N:28][CH:29]=[CH:30][N:31]=1)([CH3:24])([CH3:23])[CH3:22].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCl.C(OCC)(=O)C>[C:21]([O:25][C:26]1[C:27]([CH2:32][N:2]2[CH2:3][CH2:4][CH:5]([C:8](=[O:20])[CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:16]([F:18])([F:19])[F:17])[CH2:6][CH2:7]2)=[N:28][CH:29]=[CH:30][N:31]=1)([CH3:24])([CH3:23])[CH3:22]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
After suspending 200 mg of 1-(piperidin-4-yl)-2-[2-(trifluoromethyl)phenyl]ethanone hydrochloride in 2 ml of dichloromethane, a solution of 140 mg of 3-tert-butoxypyrazine-2-carboxaldehyde in dichloromethane (2 ml) and 207 mg of sodium triacetoxyborohydride were added while stirring, and the stirring was continued overnight at room temperature. A 1N sodium hydroxide solution was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (249 mg, 88% yield).
Workup
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-f258e53441bb4ada9186d6e1f800439d
- Source dataset
- uspto-grants-2006_02
- Patent number
- US06995144B2
Reaction notes
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