Cornforth reagent → 3-(9,10-Didehydro-6-methyl-14-nitro-8alpha-ergolinyl)-1,1-diethylurea

HRID 35214

Reaktionsgleichung

Reaktionsgleichung von HRID 35214
[CH3:1][N:2]1[C@H:16]2[C:6]([C:7]3[CH:8]=[CH:9][C:10]([N+:18]([O-:20])=[O:19])=[C:11]4[C:17]=3[CH:14]([CH2:15]2)[CH2:13][NH:12]4)=[CH:5][C@H:4]([NH:21][C:22](=[O:28])[N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[CH2:3]1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl.O>[CH3:1][N:2]1[C@H:16]2[C:6]([C:7]3[CH:8]=[CH:9][C:10]([N+:18]([O-:20])=[O:19])=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[CH:13][NH:12]4)=[CH:5][C@H:4]([NH:21][C:22](=[O:28])[N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[CH2:3]1

Komponenten

5

Edukt 2

HCID 2724130Cornforth reagentHCID 867423503-(9,10-Didehydro-2,3-dihydro-6-methyl-14-nitro-8alpha-ergolinyl)-1,1-diethylurea

Produkt 1

HCID 133749593-(9,10-Didehydro-6-methyl-14-nitro-8alpha-ergolinyl)-1,1-diethylureaAusbeute 46,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution is prepared from 150 mg of 3-(9,10-didehydro-2,3-dihydro-6-methyl-14-nitro-8α-ergolinyl)-1,1-diethylurea in 5 ml of methylene chloride; 250 mg of pyridinium dichromate, dissolved in 2 ml of methylene chloride, is added to the reaction mixture and the latter is agitated for one hour at room temperature. Then the mixture is diluted with water, extracted by shaking with methylene chloride, the organic phase is dried and evaporated. The residue is chromatographed on silica gel with methylene chloride/methanol (5%), thus obtaining 70 mg of 3-(9,10-didehydro-6-methyl-14-nitro-8α-ergolinyl)-1,1-diethylurea.

Aufarbeitung

  1. additionis added to the reaction mixture
  2. extractionextracted
  3. stirringby shaking with methylene chloride
  4. customthe organic phase is dried
  5. customevaporated
  6. customThe residue is chromatographed on silica gel with methylene chloride/methanol (5%)

Quellen und Nachweise

ORD-Eintrag
ord-ccae881c61ab40a7ad74fdb1aa4f7210
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04766128

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