Methanol → 4-benzyloxy-1-(4-{[(3S)-1-cyclopentyl-3-pyrrolidinyl]-oxy}phenyl)-1H-pyridin-2-one

HRID 15036

Reaktionsgleichung

Reaktionsgleichung von HRID 15036
[C:1]1(=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.CO.[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][N:20]([C:23]2[CH:28]=[CH:27][C:26]([O:29][C@H:30]3[CH2:34][CH2:33][NH:32][CH2:31]3)=[CH:25][CH:24]=2)[C:19](=[O:35])[CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(OCC)(=O)C>[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][N:20]([C:23]2[CH:28]=[CH:27][C:26]([O:29][C@H:30]3[CH2:34][CH2:33][N:32]([CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH2:31]3)=[CH:25][CH:24]=2)[C:19](=[O:35])[CH:18]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 8452CyclopentanoneHCID 684307174-benzyloxy-1-{4-[(3S)-3-pyrrolidinyloxy]phenyl}-1H-pyridin-2-one

Produkt 1

HCID 589648874-benzyloxy-1-(4-{[(3S)-1-cyclopentyl-3-pyrrolidinyl]-oxy}phenyl)-1H-pyridin-2-oneAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Cyclopentanone (0.017 mL, 0.186 mmol) and a 0.3 mol Zn[B(CN)H3]2 methanol solution (0.4 mL, 0.12 mmol, prepared from ZnCl2 and NaB(CN)H3) were added to a methanol solution (1 mL) of 4-benzyloxy-1-{4-[(3S)-3-pyrrolidinyloxy]phenyl}-1H-pyridin-2-one (45 mg, 0.124 mmol) and sired at room temperature for an hour. Ethyl acetate was added to the reaction liquid, which was then washed with saturated aqueous sodium bicarbonate solution and saturated brine, and dried over anhydrous potassium carbonate. The solvent was concentrated under reduced pressure and the resulting residue was purified on silica gel chromatography (C-300; methanol:chloroform=1:10) to provide the title compound (28.2 mg, 53%).

Aufarbeitung

  1. waitsired at room temperature for an hour
  2. washwas then washed with saturated aqueous sodium bicarbonate solution and saturated brine
  3. dry with materialdried over anhydrous potassium carbonate
  4. concentrationThe solvent was concentrated under reduced pressure
  5. customthe resulting residue was purified on silica gel chromatography (C-300; methanol:chloroform=1:10)

Quellen und Nachweise

ORD-Eintrag
ord-256b9f0733d545b8b8f0ddf87a008d52
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732456B2

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