Sodium Hydroxide → 1-[1-(3-tert-Butoxy-2-pyrazinylmethyl)piperidin-4-yl]-2-(2-methylphenyl)ethanone

HRID 606214Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 606214
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:11].[C:18]([O:22][C:23]1[C:24]([CH:29]=O)=[N:25][CH:26]=[CH:27][N:28]=1)([CH3:21])([CH3:20])[CH3:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCl>[C:18]([O:22][C:23]1[C:24]([CH2:29][N:15]2[CH2:14][CH2:13][CH:12]([C:10](=[O:11])[CH2:9][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[CH3:2])[CH2:17][CH2:16]2)=[N:25][CH:26]=[CH:27][N:28]=1)([CH3:21])([CH3:20])[CH3:19]

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 222482803-(tert-Butoxy)pyrazine-2-carbaldehydeHCID 222484752-(2-Methylphenyl)-1-(piperidin-4-yl)ethanone hydrochloride

Produkt 1

HCID 222479841-[1-(3-tert-Butoxy-2-pyrazinylmethyl)piperidin-4-yl]-2-(2-methylphenyl)ethanoneAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

After suspending 150 mg of 2-(2-methylphenyl)-1-(piperidin-4-yl)ethanone hydrochloride in 3 ml of dichloromethane, 128 mg of 3-tert-butoxypyrazine-2-carboxaldehyde and 188 mg of sodium triacetoxyborohydride were added while stirring on ice, and the stirring was continued overnight at room temperature. A 1N sodium hydroxide solution was added to the reaction mixture to render it alkaline, and then 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 NH silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (153 mg, 68% yield).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-40aa8cfdb4b743e99255bb84d5a21a2c
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915274B2

Notizen zur Reaktion

Wird geladen…