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Cesium carbonate → (+)[N-(Benzyloxycarbonyl)morphinan-3-yloxy]methyl isopropyl carbonate

HRID 1924435
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1924435
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C@H:7]3[N:18]([C:19]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:20])[CH2:17][CH2:16][C@@:13]4([C:14]=2[CH:15]=1)[C@H:8]3[CH2:9][CH2:10][CH2:11][CH2:12]4.C(=O)([O-])[O-].[Cs+].[Cs+].[C:35](=[O:43])([O:39][CH:40]([CH3:42])[CH3:41])[O:36][CH2:37]I>CC(C)=O>[C:35](=[O:43])([O:39][CH:40]([CH3:42])[CH3:41])[O:36][CH2:37][O:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C@H:7]3[N:18]([C:19]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:20])[CH2:17][CH2:16][C@@:13]4([C:14]=2[CH:15]=1)[C@H:8]3[CH2:9][CH2:10][CH2:11][CH2:12]4
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 15870216Iodomethyl propan-2-yl carbonate2×HCID 538511903-hydroxy-N-(benzyloxycarbonyl)morphinan

Produkt 1

HCID 67519177(+)[N-(Benzyloxycarbonyl)morphinan-3-yloxy]methyl isopropyl carbonateAusbeute 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180
Acetone
Lösungsmittel

Versuchsvorschrift

To (+)-3-hydroxy-N-(benzyloxycarbonyl)morphinan (33.0 g, 87.4 mmol) and cesium carbonate (28.5 g, 87.4 mmol) in acetone (450 mL) was added iodomethyl isopropyl carbonate (21.3 g, 87.4 mmol) (see Rigel Pharmaceuticals, Inc. US2006/247287 A1, Appl.; US2006-381215 (2006 May 2)) at room temperature. The reaction mixture was stirred vigorously at room temperature overnight. The acetone was then removed by rotary evaporation under vacuum. To the residue was added saturated NaHCO3 solution. The mixture was extracted with EtOAc (300 mL×2). The combined organics were washed with 1N HCl solution (300 mL), dried over MgSO4, filtered, and evaporated under vacuum to provide the title compound (42.0 g, 97%) as a yellow gum.

Aufarbeitung

  1. customThe acetone was then removed by rotary evaporation under vacuum
  2. additionTo the residue was added saturated NaHCO3 solution
  3. extractionThe mixture was extracted with EtOAc (300 mL×2)
  4. washThe combined organics were washed with 1N HCl solution (300 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c08443d89ddb4993a5abc08c75d52435
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08178551B2

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