Ethyl Acetate → 6-(Di-pyridin-2-yl-amino)-hexanoic acid methyl ester

HRID 404134

Reaktionsgleichung

[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23].CCOC(C)=O>CN(C=O)C.[Cl-].[Na+].O>[CH3:25][O:24][C:22](=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][N:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

NaH (112 mg, 2.92 mmol) was added to di-pyridin-2-yl-amine (500 mg, 2.92 mmol) in DMF (10 mL) at rt. After 10 min, KI (485 mg, 2.92 mmol) and methyl 6-bromohexanoate, I (0.464 mL, 2.92 mmol) were added, and the reaction mixture was stirred at 90° C. for 21 h. Brine (200 mL) and EtOAc (200 mL) were then added, the phases were separated, and the aqueous phase was extracted with EtOAc (100 mL). The organic phases were combined, dried over MgSO4, filtered, and subsequently evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using CH2Cl2/MeOH (100:0.5 to 100:1) as eluant to furnish II as a colourless oil (206 mg, 24%).

Aufarbeitung

customthe phases were separated
extractionthe aqueous phase was extracted with EtOAc (100 mL)
dry with materialdried over MgSO4
filtrationfiltered
customsubsequently evaporated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-9a11980996a44e3fa56ecda51bb47bfd
Quelldatensatz: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08748458B2

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