Reaktion #64130

Reaktionsgleichung

water

sodium hydroxide

water

8alpha-(3,3-diethylureido)-2,6-dimethyl-ergoline-13-carbaldehyde

lithium aluminum hydride

→

1,1-Diethyl-3-(2,6-dimethyl-13-hydroxymethyl-8alpha-ergolinyl)-urea

Lösungsmittel

chloroform

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture is cooled off in an ice bath
2. 2
   Filtrationthe precipitate is filtered off
3. 3
   Sonstigethe filtrate is evaporated to dryness
4. 4
   SonstigeThe residue is chromatographed on silica gel with dichloromethane/methanol
5. 5
   Sonstige243 mg of alcohol, which crystallizes from ethyl acetate
6. 6
   Sonstigeis isolated

Vorschrift

370 mg of 8alpha-(3,3-diethylureido)-2,6-dimethyl-ergoline-13-carbaldehyde (1 mmol) is dissolved in 50 ml of tetrahydrofuran and reduced with 200 mg of lithium aluminum hydride at room temperature for 1 hour. The mixture is cooled off in an ice bath and mixed in succession with 0.2 ml of water, 0.2 ml of 15% sodium hydroxide solution and 0.6 ml of water, the precipitate is filtered off and the filtrate is evaporated to dryness. The residue is chromatographed on silica gel with dichloromethane/methanol. 243 mg of alcohol, which crystallizes from ethyl acetate, is isolated. Yield 166 mg (44% of theory), [α]D =+6° (0.5% in chloroform).

Quelle