Hydrazinecarboxaldehyde → 4-(1-Phenyl-1-(2-formylhydrazinocarbonyl)-methylene)piperidine-1-carboxylic Acid Tert-Butyl Ester

HRID 1394440Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1394440
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15](O)=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH:45]([NH:47][NH2:48])=[O:46]>CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11](=[C:14]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:15]([NH:48][NH:47][CH:45]=[O:46])=[O:16])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 12229HydrazinecarboxaldehydeHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 670464544-(1-Phenyl-1-carboxy-methylene)piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 670463754-(1-Phenyl-1-(2-formylhydrazinocarbonyl)-methylene)piperidine-1-carboxylic Acid Tert-Butyl EsterAusbeute 124,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-(1-phenyl-1-carboxy-methylene)piperidine-1-carboxylic acid tert-butyl ester (1.05 g, 3.31 mmol), EDCI (0.888 g, 4.63 mmol) and HOBt (0.626 g, 4.63 mmol) in DMF (4 mL) was stirred for 30 min at room temperature and then formic hydrazide (3.97 g, 66.2 mmol) was added. Stirring was continued for 1 h and then the mixture was poured into water and extracted with EtOAc (×3). The combined organic layers were washed (H2O ×3, brine), dried (Na2SO4) and evaporated to give the title compound (1.48 g, 97%) as a colorless oil:

Aufarbeitung

  1. stirringStirring
  2. waitwas continued for 1 h
  3. extractionextracted with EtOAc (×3)
  4. washThe combined organic layers were washed (H2O ×3, brine)
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-103677e0a53844c2b2bcdfa3e37ad66a
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07348337B2

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