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Water → HCID 86743188, Verbindung

HRID 1905371
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1905371
[C:1]([N:5]1[C:19]2[C:20]3[C:7]([CH2:8][C@@H:9]4[C@@:14]([O:21][CH3:22])([C:15]=3[CH:16]=[CH:17][CH:18]=2)[CH2:13][C@@H:12]([CH2:23][OH:24])[CH2:11][N:10]4[CH3:25])=[CH:6]1)([CH3:4])([CH3:3])[CH3:2].[S:26](Cl)([C:29]1[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=1)(=[O:28])=[O:27].O>N1C=CC=CC=1>[C:1]([N:5]1[C:19]2[C:20]3[C:7]([CH2:8][C@@H:9]4[C@@:14]([O:21][CH3:22])([C:15]=3[CH:16]=[CH:17][CH:18]=2)[CH2:13][C@@H:12]([CH2:23][O:24][S:26]([C:29]2[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH2:11][N:10]4[CH3:25])=[CH:6]1)([CH3:4])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 21156212HCID 21156212, Verbindung

Produkt 1

HCID 86743188HCID 86743188, VerbindungAusbeute 76,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel2×

Versuchsvorschrift

To a solution of 1.8 g of 1-(t-butyl)-10-methoxy-6-methyl-8β-hydroxymethyl-ergoline, prepared as described in Example 2, in 20 ml of pyridine, 2.8 g of tosyl chloride in 15 ml of pyridine were slowly added. After the addition had been completed, the mixture was stirred for about six hours and was then poured into cold water and extracted with dichloromethane. The organic layer was evaporated off and the residue was chromatographed over 18 g of silica gel using dichloromethane with increasing amounts of methanol (from 0 to 4 percent) as the eluant. 2 g of 1-(t-butyl)-10-methoxy-6-methyl-8β-tosyloxymethyl-ergoline were obtained, melting at about 150° to 152° C.

Aufarbeitung

  1. additionAfter the addition
  2. extractionextracted with dichloromethane
  3. customThe organic layer was evaporated off
  4. customthe residue was chromatographed over 18 g of silica gel

Quellen und Nachweise

ORD-Eintrag
ord-c6d6c64599cd4049a85e57074ef590a9
Quelldatensatz
uspto-grants-1989_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04843073

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