Cyclopentanethiol → HCID 59516116, Verbindung

HRID 1160555Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1160555
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH:11]1([SH:16])[CH2:15][CH2:14][CH2:13][CH2:12]1.Cl[C:18]1[N:22]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([O:31][CH3:32])=[O:30])=[CH:25][CH:24]=2)[N:21]=[CH:20][C:19]=1[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34]>CN(C=O)C.CCOC(C)=O>[CH:11]1([S:16][C:18]2[N:22]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([O:31][CH3:32])=[O:30])=[CH:25][CH:24]=3)[N:21]=[CH:20][C:19]=2[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:15][CH2:14][CH2:13][CH2:12]1

Komponenten

6

Edukt 3

HCID 15510CyclopentanethiolHCID 2724254Sodium bis(trimethylsilyl)amideHCID 57437894Tert-butyl 5-chloro-1-(4-methoxycarbonylphenyl)pyrazole-4-carboxylate

Produkt 1

HCID 59516116HCID 59516116, VerbindungAusbeute 57,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Sodium bis(trimethylsilyl)amide (7.13 mL, 7.13 mmol) was added dropwise to cyclopentanethiol (0.761 mL, 7.13 mmol) in DMF (25 mL) under nitrogen. The resulting solution was stiffed at 20° C. for 30 minutes. A solution of tert-butyl 5-chloro-1-(4-(methoxycarbonyl)phenyl)-1H-pyrazole-4-carboxylate (Intermediate#9) (2 g, 5.94 mmol) in DMF (10 mL) was then added dropwise and the resulting mixture was stirred at 20° C. for 2 hours. The reaction mixture was diluted with EtOAc (200 mL), and washed sequentially with water (4×50 mL) and saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 25% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford tert-butyl 5-(cyclopentylthio)-1-(4-(methoxycarbonyl)phenyl)-1H-pyrazole-4-carboxylate (1.380 g, 57.7%) as a colourless oil which crystallised on standing.

Aufarbeitung

  1. washwashed sequentially with water (4×50 mL) and saturated brine (50 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customto afford crude product
  6. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 25% EtOAc in isohexane
  7. customPure fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-c41ef5cfeaff4c989ffbfabc05ba57e2
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816391B2

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