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Sodium Hydroxide → 1-[5-(Tert-butyldimethylsilanyloxymethyl)pyridin-2-yl]cyclopropylamine

HRID 76355
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 76355
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]#[N:17])=[N:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:18]([Mg]Br)[CH3:19].[OH-].[Na+]>O1CCCC1.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2([NH2:17])[CH2:19][CH2:18]2)=[N:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 542127655-(Tert-butyldimethylsilanyloxymethyl)-pyridine-2-carbonitrileHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 594069831-[5-(Tert-butyldimethylsilanyloxymethyl)pyridin-2-yl]cyclopropylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11026Titanium isopropoxide
Katalysator
HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

5-(tert-Butyldimethylsilanyloxymethyl)-pyridine-2-carbonitrile was dissolved in tetrahydrofuran (10 ml), titanium tetraisopropoxide (0.62 ml) was added thereto, and a solution of ethylmagnesium bromide in tetrahydrofuran (1 mol/l, 4.83 ml) was added dropwise. The mixture was stirred for 1 hr 30 min. To the reaction mixture was added 1N aqueous sodium hydroxide solution (6 ml) and tetrahydrofuran (20 ml) was further added, and the mixture was stirred and filtered. The filtrate was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated. The obtained residue was purified by column chromatography (Yamazen HI-FLASH™ COLUMN size 2 L, elution solvent: hexane/ethyl acetate) to give the title compound (192 mg).

Aufarbeitung

  1. additionwas further added
  2. stirringthe mixture was stirred
  3. filtrationfiltered
  4. washThe filtrate was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. customThe obtained residue was purified by column chromatography (Yamazen HI-FLASH™ COLUMN size 2 L, elution solvent: hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-06b1664afea24227bcadd9cf99f63356
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08835631B2

Notizen zur Reaktion

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