Water → 2-[1-[4-(2-Fluorophenoxymethyl)piperidino]ethyl]-3-methoxypyrazine

HRID 890109Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 890109
[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[O:4][CH2:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.[C:16]([C:19]1[C:24]([O:25][CH3:26])=[N:23][CH:22]=[CH:21][N:20]=1)(=O)[CH3:17].[BH4-].[Na+].O>CO.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].C(OCC)(=O)C>[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[O:4][CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([CH:16]([C:19]2[C:24]([O:25][CH3:26])=[N:23][CH:22]=[CH:21][N:20]=2)[CH3:17])[CH2:10][CH2:11]1

Komponenten

8

Edukt 4

HCID 962WaterHCID 5398321-(3-Methoxy-2-pyrazinyl)ethanoneHCID 4311764Sodium borohydrideHCID 171780514-[(2-Fluorophenoxy)methyl]piperidine

Produkt 1

HCID 222483652-[1-[4-(2-Fluorophenoxymethyl)piperidino]ethyl]-3-methoxypyrazineAusbeute 11 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 11026Titanium isopropoxideLösungsmittel

Versuchsvorschrift

After dissolving 1.09 g of 4-(2-fluorophenoxymethyl)piperidine in 15 ml of methanol, 1.53 ml of titanium(IV)tetraisopropoxide and 400 mg of 2-acetyl-3-methoxypyrazine [CAS No.56343-40-9] were added and the mixture was stirred overnight at room temperature. The reaction solution was cooled on ice, 118 mg of sodium borohydride was added and the mixture was stirred for 5 hours at room temperature. Water and ethyl acetate were added to the reaction solution and the mixture was filtered with celite. The filtrate was extracted with ethyl acetate and the extract was washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by NH silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (100 mg, 11% yield).

Aufarbeitung

  1. addition56343-40-9] were added
  2. additionwas added
  3. stirringthe mixture was stirred for 5 hours at room temperature
  4. filtrationthe mixture was filtered with celite
  5. extractionThe filtrate was extracted with ethyl acetate
  6. washthe extract was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by NH silica gel column chromatography (solvent: n-hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-a45d9dc0fbf3440aa4f4146b1d894018
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US06995144B2

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