Sodium Bicarbonate → 3-[4-Hydroxy-4-[(2-fluorophenyl)ethynyl)piperidino]methyl-1H-pyridin-2-one

HRID 914898Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 914898
Cl.[OH:2][C:3]1([C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[O:18]=[C:19]1[C:24]([CH:25]=O)=[CH:23][CH:22]=[CH:21][NH:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.ClCCl>[OH:2][C:3]1([C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])[CH2:4][CH2:5][N:6]([CH2:25][C:24]2[C:19](=[O:18])[NH:20][CH:21]=[CH:22][CH:23]=2)[CH2:7][CH2:8]1

Komponenten

7

Edukt 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 70621962-Oxo-1,2-dihydropyridine-3-carbaldehydeHCID 222484404-Hydroxy-4-[(2-fluorophenyl)ethynyl]piperidine hydrochloride

Produkt 1

HCID 222484353-[4-Hydroxy-4-[(2-fluorophenyl)ethynyl)piperidino]methyl-1H-pyridin-2-oneAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

After then adding 253 mg of the 4-hydroxy-4-[(2-fluorophenyl)ethynyl]piperidine hydrochloride to 10 ml of dichloromethane, 158 mg of 2-oxo-1,2-dihydropyridine-3-carboxaldehyde was added and the mixture was stirred for 10 minutes at room temperature. Next, 315 mg of sodium triacetoxyborohydride was added and the mixture was stirred overnight at room temperature. Saturated aqueous sodium bicarbonate solution was added to the reaction mixture and extraction was performed with ethyl acetate. After drying the organic layer over magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by NH silica gel column chromatography to obtain the title compound (32 mg, 10% yield).

Aufarbeitung

  1. additionwas added
  2. stirringthe mixture was stirred overnight at room temperature
  3. dry with materialAfter drying the organic layer over magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by NH silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6062b52183ae45c78b642ab9c88d928b
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265108B2

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