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Sodium borohydride → Methyl 6-(dibenzylamino)-3-(3-methoxy-3-oxopropyl)pyridine-2-carboxylate

HRID 887757
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 887757
[CH2:1]([N:8]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:9]1[N:14]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[C:12](/[CH:19]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.[Cl-].[NH4+].O.O.O.O.O.O.[Ni](Cl)Cl>[CH2:25]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[N:14]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[C:12]([CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:11][CH:10]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 4311764Sodium borohydrideHCID 59145876methyl 6-(dibenzylamino)-3-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]pyridine-2-carboxylate

Produkt 1

HCID 59145865Methyl 6-(dibenzylamino)-3-(3-methoxy-3-oxopropyl)pyridine-2-carboxylateAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11791229Dichloronickel;hexahydrateKatalysator
HCID 887
Methanol
Lösungsmittel
HCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

To a solution of methyl 6-(dibenzylamino)-3-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]pyridine-2-carboxylate (2.60 g, 6.24 mmol) and nickel(II) chloride hexahydrate (891 mg, 3.75 mmol) in methanol (62 mL) was added sodium tetrahydroborate (472 mg, 12.5 mmol) under ice-cooling, and the mixture was stirred for 5 min. The reaction solution was diluted with saturated aqueous ammonium chloride solution, and the organic solvent was evaporated under reduced pressure. The residue was diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→30/70) to give the title compound (2.24 g, yield 86%).

Aufarbeitung

  1. temperaturecooling
  2. customthe organic solvent was evaporated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→30/70)

Quellen und Nachweise

ORD-Eintrag
ord-42093bc147ea48df87675a44b529ea9e
Quelldatensatz
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08247429B2

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