Hydrazinium chloride → HCID 178469860, Verbindung

HRID 505632Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505632
C[N:2]([CH:4]=[C:5]1[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][CH:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:6]1=O)C.Cl.[NH2:25]N>CCO>[N:25]1[NH:2][CH:4]=[C:5]2[C:6]=1[CH:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10]2

Komponenten

4

Edukt 2

HCID 115031Hydrazinium chlorideHCID 684658601-Tert-butyl 3-ethyl 5-((dimethylamino)methylene)-4-oxopiperidine-1,3-dicarboxylate

Produkt 1

HCID 178469860HCID 178469860, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of enaminoketone 3b (327 mg, 1.00 mmol) in abs. EtOH (10 mL) was cooled to 0° C. and hydrazine monohydrogen chloride was added in one portion. The mixture was stirred for 18 h during which time the temperature reached rt after 2 h. The mixture was concentrated and the residue partitioned with deionized H2O and EtOAc. The organic layer was removed and the aqueous portion extracted with EtOAc (2×). The combined EtOAc portions were washed with brine, dried over MgSO4 and filtered through a SiO2 plug capped with a MgSO4 layer (EtOAc for elution). The solution was concentrated give the title compound 4b as a brittle white foam crushed to a white solid; 253 mg, 87%, MS m/z 240.0, 194.0 (ESI+, M−tBu, M−Boc).

Aufarbeitung

  1. waitreached rt after 2 h
  2. concentrationThe mixture was concentrated
  3. customthe residue partitioned with deionized H2O and EtOAc
  4. customThe organic layer was removed
  5. extractionthe aqueous portion extracted with EtOAc (2×)
  6. washThe combined EtOAc portions were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered through a SiO2 plug
  9. customcapped with a MgSO4 layer (EtOAc for elution)
  10. concentrationThe solution was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-78ff8f8c81bd4e489a8e338a8c6bb5c4
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781474B2

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