Sodium Hydroxide → 2-[(Cyclopentylmethyl)(ethyl)amino]-6-ethylnicotinaldehyde

HRID 1710868Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1710868
[CH:1]1([CH2:6][N:7]([CH2:18][CH3:19])[C:8]2[C:13]([C:14]#N)=[CH:12][CH:11]=[C:10]([CH2:16][CH3:17])[N:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].C([Al+]CC(C)C)C(C)C.[OH-:30].[Na+]>ClCCl>[CH:1]1([CH2:6][N:7]([CH2:18][CH3:19])[C:8]2[N:9]=[C:10]([CH2:16][CH3:17])[CH:11]=[CH:12][C:13]=2[CH:14]=[O:30])[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 21225700Diisobutylaluminumhydride2×HCID 673913322-[(Cyclopentylmethyl)(ethyl)amino]-6-ethylpyridine-3-carbonitrile

Produkt 1

HCID 866284322-[(Cyclopentylmethyl)(ethyl)amino]-6-ethylnicotinaldehydeAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2-[(cyclopentylmethyl)(ethyl)amino]-6-ethylpyridine-3-carbonitrile (484 mg, 1.87 mmol) in dichloromethane (5 mL) was added with diisobutylaluminum hydride (0.99 M solution in toluene, 1.99 mL, 1.97 mmol) at −78° C., and the mixture was stirred at the same temperature for 4 hours. The mixture was further added with diisobutylaluminum hydride (0.99 M solution in toluene, 0.2 mL, 0.198 mmol) at the same temperature, and the mixture was stirred at the same temperature for 45 minutes. Then, the mixture was added with 2 M aqueous sodium hydroxide, stirred at room temperature for 30 minutes, and extracted with chloroform. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1) to obtain 2-[(cyclopentylmethyl)(ethyl)amino]-6-ethylnicotinaldehyde (233 mg, 48%) as yellow oil.

Aufarbeitung

  1. stirringthe mixture was stirred at the same temperature for 45 minutes
  2. stirringstirred at room temperature for 30 minutes
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1)

Quellen und Nachweise

ORD-Eintrag
ord-47aec1b27f454d44800ac3b49cb67f30
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790737B2

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