Tetrahydrofuran → tert-butyl 4-[2-(4-oxo-2-phenyl-4,5-dihydro-2H-pyrazolo[3,4-c]quinolin-1-yl)ethyl]piperidine-1-carboxylate

HRID 1095349Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1095349
[C:1]1([N:7]2[C:19](=O)[C:18]3[C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[NH:11][CH2:10][C:9]=3[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)CCN(C)C.C([Li])CCC.I[CH2:35][CH2:36][CH:37]1[CH2:42][CH2:41][N:40]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:39][CH2:38]1.[O:50]1CCCC1>C(#N)C>[O:50]=[C:10]1[C:9]2=[N:8][N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:19]([CH2:35][CH2:36][CH:37]3[CH2:42][CH2:41][N:40]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:39][CH2:38]3)=[C:18]2[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH:11]1

Komponenten

7

Edukt 5

HCID 8028TetrahydrofuranHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 9974426Tert-butyl 4-(2-iodoethyl)piperidine-1-carboxylateHCID 57454660HCID 57454660, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 57446216tert-butyl 4-[2-(4-oxo-2-phenyl-4,5-dihydro-2H-pyrazolo[3,4-c]quinolin-1-yl)ethyl]piperidine-1-carboxylateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Under a nitrogen atmosphere, a mixture of 2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinoline-one (1.76 g, 6.76 mmol), N,N,N′,N′-tetramethylethylenediamine (4.5 mL), and tetrahydrofuran (75 mL) was chilled to 0° C. A solution of n-butyllithium in hexanes (8.1 mL of 2.5 M) was added dropwise. After the addition was complete the reaction mixture was stirred for 5 minutes at 0° C. and then cooled to −78° C. To the cooled solution was added tert-butyl 4-(2-iodoethyl)piperidine-1-carboxylate (3.0 g, 8.8 mmol). The reaction mixture was warmed to ambient temperature and stirred for 30 minutes before quenching with saturated aqueous ammonium chloride. The aqueous layer was extracted with chloroform. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford a yellow oil, The yellow oil was stirred in acetonitrile and filtered to provide 1.4 g (75% pure) of tert-butyl 4-[2-(4-oxo-2-phenyl-4,5-dihydro-2H-pyrazolo[3,4-c]quinolin-1-yl)ethyl]piperidine-1-carboxylate as a tan solid.

Aufarbeitung

  1. additionAfter the addition
  2. temperaturecooled to −78° C
  3. temperatureThe reaction mixture was warmed to ambient temperature
  4. stirringstirred for 30 minutes
  5. custombefore quenching with saturated aqueous ammonium chloride
  6. extractionThe aqueous layer was extracted with chloroform
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto afford a yellow oil
  11. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-6a1d59d683cb452faa1c5bda4123acdc
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138173B2

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