Hydrazine → 1'-(tert-Butoxycarbonyl)-3-oxo-2,3,4,5-tetrahydrospiro[cyclopentapyrazole-6(1H),4'-piperidine]

HRID 8754

Reaktionsgleichung

Reaktionsgleichung von HRID 8754
C[O:2][C:3]([CH:5]1[CH2:9][CH2:8][C:7]2([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[C:6]1=O)=O.[NH2:23][NH2:24]>C1(C)C=CC=CC=1>[C:18]([O:17][C:15]([N:12]1[CH2:13][CH2:14][C:7]2([C:6]3[NH:24][NH:23][C:3](=[O:2])[C:5]=3[CH2:9][CH2:8]2)[CH2:10][CH2:11]1)=[O:16])([CH3:21])([CH3:20])[CH3:19]

Komponenten

4

Edukt 2

HCID 9321HydrazineHCID 219838978-tert-Butyl 2-methyl 1-oxo-8-azaspiro[4.5]decane-2,8-dicarboxylate

Produkt 1

HCID 219839441'-(tert-Butoxycarbonyl)-3-oxo-2,3,4,5-tetrahydrospiro[cyclopentapyrazole-6(1H),4'-piperidine]Ausbeute 61,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 2-(methoxycarbonyl)-1-oxo-8-azaspiro[4.5]decane-8-carboxate from Procedure 1, Step F (0.448 g, 1.46 mmol) in toluene (15 mL) was added hydrazine (0.084 mL, 1.72 mmol). The reaction mixture was refluxed for 12 h, concentrated and the residue was purified by flash chromatography eluting with 5% MeOH/dichloromethane and 0.1% triethylamine to give the title compound (0.263 g). MS/EI (acetonitrile/water): m/z 294.3 retention time=2.0 min.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 12 h
  2. concentrationconcentrated
  3. customthe residue was purified by flash chromatography
  4. washeluting with 5% MeOH/dichloromethane and 0.1% triethylamine

Quellen und Nachweise

ORD-Eintrag
ord-701f21b2c1d643e889f13cae87e55dcf
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091211B2

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