Triethylamine → HCID 57743093, Verbindung

HRID 1926860Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1926860
[NH2:1][C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.Cl.[NH2:11][CH2:12][CH:13]([CH2:20][CH2:21][CH3:22])[CH2:14][C:15](OCC)=[O:16].C(N(CC)CC)C.[BH4-].[Na+]>CCO>[NH2:1][C:2]1[C:3]([CH2:4][N:11]2[CH2:12][CH:13]([CH2:20][CH2:21][CH3:22])[CH2:14][C:15]2=[O:16])=[CH:6][CH:7]=[CH:8][N:9]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 7376333-Pyridinecarboxaldehyde, 2-amino-HCID 4311764Sodium borohydrideHCID 53629151HCID 53629151, Verbindung

Produkt 1

HCID 57743093HCID 57743093, VerbindungAusbeute 8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2-aminonicotinaldehyde x282 (8.19 mmol, 1 eq, 1 g) in 10 ml of EtOH, is added ethyl 3-(aminomethyl)hexanoate hydrochloride x31 (9.83 mmol, 1.2 eq, 2.06 g) and the resulting solution is stirred at room temperature for 1 h30. Then, triethylamine (9.0 mmol, 1.1 eq, 909 mg) is added and the mixture is stirred during 0.5 hour. Sodium borohydride is then added (9.83 mmol, 1.2 eq, 372 mg). The resulting mixture is stirred at room temperature for 20 hours, heated at 55° C. for 21 hours and then overnight at room temperature. Volatiles are removed under vacuum and CH2Cl2 (50 ml) and water (25 ml) are added. The organic layer is washed with water (25 ml) and dried over MgSO4. After filtration, volatiles are removed under reduced pressure. The crude product is purified by chromatography on silicagel (CH2Cl2/MeOH/NH4OH 98/2/0.2 (v/v/v)) and recrystallized in AcOEt to afford 1-[(2-aminopyridin-3-yl)methyl]-4-propylpyrrolidin-2-one 230 as a white solid (152 mg).

Aufarbeitung

  1. stirringthe mixture is stirred during 0.5 hour
  2. stirringThe resulting mixture is stirred at room temperature for 20 hours
  3. temperatureheated at 55° C. for 21 hours
  4. customovernight
  5. customat room temperature
  6. customVolatiles are removed under vacuum and CH2Cl2 (50 ml) and water (25 ml)
  7. additionare added
  8. washThe organic layer is washed with water (25 ml)
  9. dry with materialdried over MgSO4
  10. filtrationAfter filtration, volatiles
  11. customare removed under reduced pressure
  12. customThe crude product is purified by chromatography on silicagel (CH2Cl2/MeOH/NH4OH 98/2/0.2 (v/v/v))
  13. customrecrystallized in AcOEt

Quellen und Nachweise

ORD-Eintrag
ord-34d9a1322aad420b8f570eacbfe48ff3
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183241B2

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