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Cesium carbonate → ethyl 3-[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]benzoate

HRID 1691730
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1691730
O1CCOCC1.[C:7]([O:11][C:12](=[O:39])[N:13]([C@@H:27]([C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1)[CH3:28])[CH2:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH:16]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:10])([CH3:9])[CH3:8].I[C:41]1[CH:42]=[C:43]([CH:49]=[CH:50][CH:51]=1)[C:44]([O:46][CH2:47][CH3:48])=[O:45].C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.C(OCC)(=O)C.C(O)(C)(C)C>[C:7]([O:11][C:12]([N:13]([CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:41]2[CH:42]=[C:43]([CH:49]=[CH:50][CH:51]=2)[C:44]([O:46][CH2:47][CH3:48])=[O:45])[CH2:17][CH:16]1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C@@H:27]([C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1)[CH3:28])=[O:39])([CH3:8])([CH3:9])[CH3:10]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 10796Cesium carbonateHCID 312751,4-Dioxane2×HCID 143542Ethyl 3-iodobenzoateHCID 59178521HCID 59178521, Verbindung

Produkt 1

HCID 66906240ethyl 3-[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]benzoateAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel

4
HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylKatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 6386tert-ButanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of 2.3 mg of tris(dibenzylideneacetone)dipalladium(0), 1.9 mg of 2-(dicyclohexylphosphino)-2′-(dimethylamino)biphenyl, and 0.5 mL of 1,4-dioxane were added 100 mg of tert-butyl[(1R)-1-(1-naphthyl)ethyl][(3-phenylpiperidin-4-yl)methyl]carbamate, 83.8 mg of ethyl 3-iodobenzoate, 105 mg of cesium carbonate, 1.0 mL of 1,4-dioxane, and 1.5 mL of t-butanol, followed by stirring at 100° C. overnight. After cooling to room temperature, to the reaction mixture was added ethyl acetate, the insolubles were removed, and the solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 108 mg of ethyl 3-[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]benzoate as a pale yellow foamy substance. ESI+: 593

Aufarbeitung

  1. temperatureAfter cooling to room temperature, to the reaction mixture
  2. customthe insolubles were removed
  3. customthe solvent was removed by distillation under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-73d9afbf22ea4b9b8363dc939f337a8d
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08153658B2

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