Water → 6-[(1-Cyclobutylpiperidin-4-yl)oxy]nicotinaldehyde

HRID 2422673Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2422673
[CH:1]1([N:5]2[CH2:10][CH2:9][CH:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([CH:18]=C)=[CH:14][N:13]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.I([O-])(=O)(=O)=[O:21].[Na+].C1COCC1.O>C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[CH:1]1([N:5]2[CH2:10][CH2:9][CH:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([CH:18]=[O:21])=[CH:14][N:13]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 23667635Sodium periodateHCID 672459142-[(1-Cyclobutylpiperidin-4-yl)oxy]-5-vinylpyridine

Produkt 1

HCID 866244636-[(1-Cyclobutylpiperidin-4-yl)oxy]nicotinaldehydeAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-[(1-cyclobutylpiperidin-4-yl)oxy]-5-vinylpyridine (2.59 g, 10 mmol) and sodium periodate (10.7 g, 50 mmol) were stirred in a mixed solvent of THF (10 mL) and water (10 mL) at room temperature. Osmium tetroxide (0.2 M in t-BuOH, 1 mL) was dropwise added to the reaction solution, and stirred at room temperature for 24 hours. The reaction solution was diluted with ethyl acetate, washed with aqueous 1 N sodium hydroxide solution, aqueous saturated sodium thiosulfate solution and saturated saline water in that order, and the organic layer was dried with magnesium sulfate. The solvent was evaporated off, and the residue was purified through silica gel column chromatography (chloroform/methanol=9/1) to obtain the intended compound (1.04 g, 40%) as a brown solid.

Aufarbeitung

  1. washwashed with aqueous 1 N sodium hydroxide solution, aqueous saturated sodium thiosulfate solution and saturated saline water in that order
  2. dry with materialthe organic layer was dried with magnesium sulfate
  3. customThe solvent was evaporated off
  4. customthe residue was purified through silica gel column chromatography (chloroform/methanol=9/1)

Quellen und Nachweise

ORD-Eintrag
ord-858093b1bd234678a8d911cd100b31cf
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960394B2

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