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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-(1-Phenyl-1-hydrazinocarbonyl-methylene)piperidine-1-carboxylic acid tert-butyl ester

HRID 606759
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 606759
[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:42]=[N:41]C=2C=1.O.NN>CN(C=O)C.O>[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]([NH:41][NH2:42])=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
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Komponenten

7

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 24654Hydrazine hydrate (1:1)HCID 757711-HydroxybenzotriazoleHCID 670464544-(1-Phenyl-1-carboxy-methylene)piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 116169104-(1-Phenyl-1-hydrazinocarbonyl-methylene)piperidine-1-carboxylic acid tert-butyl esterAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-(1-phenyl-1-carboxy-methylene)piperidine-1-carboxylic acid tert-butyl ester (0.153 g, 0.048 mol), EDCI (0.113 g, 0.059 mol), and HOBt (0.081 g, 0.060 mol) in DMF (3 mL) was stirred for 30 min at room temperature and then hydrazine hydrate (1.0 mL) was added. Stirring was continued for 12 h and then the mixture was poured into water and extracted with EtOAc (×3). The combined organic layers were washed, (H2O ×5, brine) and dried (Na2SO4). The solvent was removed in vacuo and the residue was purified by preparative HPLC to give the title compound (0.147 g, 92%) as a colorless oil:

Aufarbeitung

  1. stirringStirring
  2. waitwas continued for 12 h
  3. extractionextracted with EtOAc (×3)
  4. washThe combined organic layers were washed
  5. dry with material(H2O ×5, brine) and dried (Na2SO4)
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-99f16274aacb486f98a192cd5dc0b082
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07915283B2

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