Boron trifluoride etherate → 6,7-Dihydroxy-2-(5-isoquinolinesulfonyl)-3-[(4-phenylpiperazinyl)methyl]-1,2,3,4-tetrahydroisoquinoline

HRID 1090562

Reaktionsgleichung

Reaktionsgleichung von HRID 1090562
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19]CC1C=CC=CC=1)[CH2:15][N:14]([S:27]([C:30]1[C:31]3[CH:32]=[CH:33][N:34]=[CH:35][C:36]=3[CH:37]=[CH:38][CH:39]=1)(=[O:29])=[O:28])[CH:13]([CH2:40][N:41]1[CH2:46][CH2:45][N:44]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[CH2:43][CH2:42]1)[CH2:12]2)C1C=CC=CC=1.C(S)CS.B(F)(F)F.C(OCC)C.C(=O)(O)[O-].[Na+]>>[OH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[OH:19])[CH2:15][N:14]([S:27]([C:30]1[C:31]3[CH:32]=[CH:33][N:34]=[CH:35][C:36]=3[CH:37]=[CH:38][CH:39]=1)(=[O:29])=[O:28])[CH:13]([CH2:40][N:41]1[CH2:42][CH2:43][N:44]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[CH2:45][CH2:46]1)[CH2:12]2

Komponenten

5

Edukt 4

HCID 8000Boron trifluoride etherateHCID 109021,2-EthanedithiolHCID 516892Sodium BicarbonateHCID 197962306,7-Dibenzyloxy-2-(5-isoquinolinesulfonyl)-3-[(4-phenylpiperazinyl)methyl]-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 197963856,7-Dihydroxy-2-(5-isoquinolinesulfonyl)-3-[(4-phenylpiperazinyl)methyl]-1,2,3,4-tetrahydroisoquinolineAusbeute 90,9 %

Versuchsvorschrift

To 314 mg of the amorphous compound obtained in Example 9, were added 2 ml of 1,2-ethanedithiol and 1 ml of boron trifluoride/ethyl ether, and the mixture was stirred at a room temperature for 18 hours. After the addition of saturated sodium bicarbonate aqueous solution, the reaction mixture was extracted twice with a mixture of chloroform and methanol (1:1), and the extract was dried over magnesium sulfate and concentrated under a reduced pressure to obtain a residue, which was then applied to a silica gel column and eluted with chloroform/methanol (50:1 to 20:1) to obtain 213 mg of the title compound in a colorless amorphous form.

Aufarbeitung

  1. extractionthe reaction mixture was extracted twice with a mixture of chloroform and methanol (1:1)
  2. dry with materialthe extract was dried over magnesium sulfate
  3. concentrationconcentrated under a reduced pressure
  4. customto obtain a residue, which
  5. washeluted with chloroform/methanol (50:1 to 20:1)

Quellen und Nachweise

ORD-Eintrag
ord-13a207f5c994479e81b22845aad5f26f
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05081246

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