(1S)-1,2,3,4-Tetrahydro-1-phenylisoquinoline → Solifenacin

HRID 1171852

Reaktionsgleichung

Reaktionsgleichung von HRID 1171852
[O-]CC.[Na+].[C:5](=[O:18])([O:9][C@@H:10]1[CH:15]2[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]2)[CH2:11]1)OCC.[C:19]1([C@H:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][CH2:27][NH:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1.CN(C=O)C>[CH:22]1[CH:21]=[CH:20][C:19]([C@@H:25]2[N:26]([C:5]([O:9][C@@H:10]3[CH:15]4[CH2:14][CH2:13][N:12]([CH2:17][CH2:16]4)[CH2:11]3)=[O:18])[CH2:27][CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:34]2=3)=[CH:24][CH:23]=1

Komponenten

6

Edukt 3

HCID 1382087(1S)-1,2,3,4-Tetrahydro-1-phenylisoquinolineHCID 2723922Sodium ethoxideHCID 38988498ethyl (R)-quinuclidin-3-yl carbonate

Produkt 1

HCID 154059SolifenacinAusbeute 12,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In a mixture of 10 ml of toluene and 0.5 ml of DMF and in the presence of 0.21 g of sodium ethoxide, 1.00 g of ethyl (R)-quinuclidin-3-yl carbonate and 1.05 g of (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline were stirred for 7 hours while evaporating the solvent, 20 ml of toluene and 20 ml of water were added thereto, and the thus obtained organic layer was washed with 20 ml of water and then mixed with 15 ml of 1 M hydrochloric acid aqueous solution. A 30 ml portion of EtOAc and 1 M sodium hydroxide aqueous solution were added to the obtained water layer. The thus obtained organic layer was dried with sodium sulfate, concentrated under a reduced pressure and then dried, and the thus obtained solid was purified by a silica gel column chromatography to obtain 0.22 g of solifenacin.

Aufarbeitung

  1. customwhile evaporating the solvent, 20 ml of toluene and 20 ml of water
  2. additionwere added
  3. washthe thus obtained organic layer was washed with 20 ml of water
  4. additionmixed with 15 ml of 1 M hydrochloric acid aqueous solution
  5. additionA 30 ml portion of EtOAc and 1 M sodium hydroxide aqueous solution were added to the obtained water layer
  6. dry with materialThe thus obtained organic layer was dried with sodium sulfate
  7. concentrationconcentrated under a reduced pressure
  8. customdried
  9. customthe thus obtained solid was purified by a silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6a8a0493e2174174ad99fdd286b8d864
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829715B2

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