Benzylethanolamine → 2-[Benzyl({3-chloro-5-[methyl(1-methylethyl)amino]pyrazin-2-yl}methyl)amino]ethanol

HRID 1877827Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1877827
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:15][C:16]1[C:17]([CH:27]=O)=[N:18][CH:19]=[C:20]([N:22]([CH3:26])[CH:23]([CH3:25])[CH3:24])[N:21]=1.[CH2:29]([NH:36][CH2:37][CH2:38][OH:39])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C.C(O)(=O)C>[CH2:29]([N:36]([CH2:27][C:17]1[C:16]([Cl:15])=[N:21][C:20]([N:22]([CH3:26])[CH:23]([CH3:24])[CH3:25])=[CH:19][N:18]=1)[CH2:37][CH2:38][OH:39])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Komponenten

8

Edukt 4

HCID 4348BenzylethanolamineHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86648985HCID 86648985, Verbindung

Produkt 1

HCID 866489842-[Benzyl({3-chloro-5-[methyl(1-methylethyl)amino]pyrazin-2-yl}methyl)amino]ethanolAusbeute 107,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Sodium triacetoxyborohydride (12.8 g) was added to a solution of 3-chloro-5-[methyl(1-methylethyl)amino]pyrazine-2-carbaldehyde (8.6 g), N-benzylethanolamine (7.3 g) and acetic acid (6.9 mL) in acetonitrile (86 mL), and the mixture was stirred at room temperature for 5 hr. To the reaction mixture were added ethyl acetate and 2M aqueous potassium carbonate solution (86 mL), and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and saturated brine, dried over magnesium sulfate, and concentrated. The residue was purified by basic silica gel column chromatography (solvent gradient: 10→30% ethyl acetate/hexane) to give the title compound (15.1 g, quantitative) as a pale-yellow oil.

Aufarbeitung

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washThe combined organic layer was washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by basic silica gel column chromatography (solvent gradient: 10→30% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-adaf3e7a199448cb90e503a57b6d6142
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314088B2

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