Ethyl bromoacetate → HCID 70424500, Verbindung

HRID 2308604Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2308604
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:8][CH2:9][C@@H:10]1[CH2:24][C@H:23]2[C@@H:13]([CH2:14][C:15]3[C:25]4[C:18](=[CH:19][CH:20]=[CH:21][C:22]2=4)[NH:17][CH:16]=3)[N:12]([CH3:26])[CH2:11]1>CN(C)C=O>[CH3:26][N:12]1[C@H:13]2[C@@H:23]([C:22]3[CH:21]=[CH:20][CH:19]=[C:18]4[C:25]=3[C:15]([CH2:14]2)=[CH:16][NH:17]4)[CH2:24][C@@H:10]([CH2:9][NH:8][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:11]1

Komponenten

4

Edukt 2

HCID 7748Ethyl bromoacetateHCID 10611049HCID 10611049, Verbindung

Produkt 1

HCID 70424500HCID 70424500, VerbindungAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of 1.3 ml of ethyl bromoacetate in 30 ml of dimethylformamide was added to a warmed solution of 6 g of 8β-aminomethyl-6-methyl-ergoline in 90 ml of dimethylformamide. At the end of the reaction, the solution was reduced in volume by evaporation in vacuo, poured into iced water and extracted with chloroform. The organic layer was removed in vacuo and the residue was purified by column chromatography on silica gel, using ethyl acetate:methanol (9:1 by volume) as eluent, to give 3.5 g of 6-methyl-8β-(N-ethoxycarbonylmethyl-aminomethyl)-ergoline (II: R1 =R2 =R3 =H, R4 =CH3, n=1, A=CHR6, R6 =H, B=CO2C2H5), m.p. 174°-176° C., after crystallization from diethyl ether. 3.5 of 6-methyl-8β-(N-ethoxycarbonylmethyl-aminomethyl)-ergoline were treated with 1.75 g of potassium cyanate, as described in Example 1, and the title compound, m.p. >300° C., was obtained in 72% yield.

Aufarbeitung

  1. customAt the end of the reaction
  2. customthe solution was reduced in volume by evaporation in vacuo
  3. additionpoured into iced water
  4. extractionextracted with chloroform
  5. customThe organic layer was removed in vacuo
  6. customthe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-29c9b51d3a5f4507989a04d6236eadcc
Quelldatensatz
uspto-grants-1987_09
Patentnummer
US04690929

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