Potassium Phosphate, Tribasic → 1-(3-Chloro-4-cyano-2-methylphenyl)-2-oxo-octahydrocyclopenta[b]-pyrrol-4-yl benzoate

HRID 15188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 15188
[C:1]([O:9][CH:10]1[CH:17]2[CH:13]([C:14](=[O:18])[NH:15][CH2:16]2)[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O:27][CH:28]1[CH:35]2[CH:31]([NH:32][C:33](=[O:36])[CH2:34]2)[CH2:30][CH2:29]1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[Cl:45][C:46]1[C:53]([CH3:54])=[C:52](I)[CH:51]=[CH:50][C:47]=1[C:48]#[N:49]>O1CCOCC1.[Cu]I>[C:1]([O:9][CH:10]1[CH:17]2[CH:13]([C:14](=[O:18])[N:15]([C:52]3[CH:51]=[CH:50][C:47]([C:48]#[N:49])=[C:46]([Cl:45])[C:53]=3[CH3:54])[CH2:16]2)[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O:27][CH:28]1[CH:35]2[CH:31]([N:32]([C:52]3[CH:51]=[CH:50][C:47]([C:48]#[N:49])=[C:46]([Cl:45])[C:53]=3[CH3:54])[C:33](=[O:36])[CH2:34]2)[CH2:30][CH2:29]1)(=[O:26])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 167319952-Chloro-4-iodo-3-methylbenzonitrileHCID 592595601-Oxo-octahydrocyclopenta[c]pyrrol-4-yl benzoateHCID 592595712-Oxo-octahydrocyclopenta[b]pyrrol-4-yl benzoate

Produkt 2

HCID 592595661-(3-Chloro-4-cyano-2-methylphenyl)-2-oxo-octahydrocyclopenta[b]-pyrrol-4-yl benzoateHCID 592595732-(3-Chloro-4-cyano-2-methylphenyl)-1-oxo-octahydrocyclopenta[c]-pyrrol-4-yl benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a vial containing mixtures of compound 1I and 1J (100 mg, 0.4 mmol) obtained from previous step in dioxane (1 mL) were added CuI (15.6 mg, 0.08 mmol), K3PO4 (174 mg, 0.82 mmol), 1,2-cyclohexyldiamine (4.7 mg, 0.08 mmol) and compound 1E (136 mg, 0.49 mmol). The vial was sealed, and heated at 110° C. for 14 hr, cooled to RT. The solid was filtered off, and filtrate was concentrated. Purification by silica gel chromatography (5% to 100% EtOAc in hexanes, then 10% methanol in EtOAc) provide the mixtures of title compounds 1K and 1L (total 98 mg) as a yellow oil. MS (ES) m/z 395 [M+H]+.

Aufarbeitung

  1. customThe vial was sealed
  2. temperaturecooled to RT
  3. filtrationThe solid was filtered off
  4. concentrationfiltrate was concentrated
  5. customPurification by silica gel chromatography (5% to 100% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-a49347e1b1dd457e81bbc1ba442e3524
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732480B2

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