Sodium Hydroxide → 1-[1-(3-Tert-butoxy-2-pyrazinylmethyl)piperidin-4-yl]-2-[2-(trifluoromethyl)phenyl]ethanone

HRID 606247Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 606247
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]

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 222482803-(tert-Butoxy)pyrazine-2-carbaldehydeHCID 222484771-(Piperidin-4-yl)-2-[2-(trifluoromethyl)phenyl)ethanone hydrochloride

Produkt 1

HCID 222484871-[1-(3-Tert-butoxy-2-pyrazinylmethyl)piperidin-4-yl]-2-[2-(trifluoromethyl)phenyl]ethanoneAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d4e105ef53f5479aa744bdf501b3d63d
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915274B2

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