Reaktion #351637

Reaktionsgleichung

4,5-dihydro-8-methoxy-1H-benz[g]indol-1-yl-propan-2-ol

triethyl-amine

sodium azide

methanesulfonyl chloride

→

(R)-1-(2-azido-propyl)-4,5-dihydro-8-methoxy-1H-benz[g]indole

Ausbeute 58.0%

Lösungsmittel

dichloromethane

diethyl ether

dimethylformamide

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at this temperature for an additional 1.5 hours
2. 2
   Waschenwashed twice with 100 ml of saturated sodium hydrogen carbonate solution each time
3. 3
   Extraktionthe combined aqueous phases were extracted once with 100 ml of diethyl ether
4. 4
   WaschenThe combined organic phases were washed with 100 ml of saturated sodium chloride solution
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Sonstigeevaporated in a vacuum
7. 7
   SonstigeThe oil obtained
8. 8
   Temperaturthe reaction mixture was heated to 60° for 15 hours
9. 9
   workup.STIRRINGwhile stirring
10. 10
    TemperaturAfter cooling
11. 11
    Extraktionextracted twice with 140 ml of diethyl ether each time
12. 12
    WaschenThe combined organic phases were washed once with 100 ml of water and once with 100 ml of saturated sodium chloride solution
13. 13
    Trocknendried over magnesium sulfate
14. 14
    Einengenthe solution was concentrated in a vacuum
15. 15
    SonstigeThe brown oil obtained
16. 16
    Sonstigewas purified by column chromatography on silica gel (toluene)

Vorschrift

1.8 ml of methanesulfonyl chloride were added dropwise while stirring to a solution, cooled to 0°, of 3 g of (S)-1-(4,5-dihydro-8-methoxy-1H-benz[g]indol-1-yl-propan-2-ol and 6.55 ml of triethyl-amine in 80 ml of dichloromethane and the mixture was stirred at this temperature for an additional 1.5 hours. The reaction mixture was subsequently diluted with 300 ml of diethyl ether, washed twice with 100 ml of saturated sodium hydrogen carbonate solution each time and the combined aqueous phases were extracted once with 100 ml of diethyl ether. The combined organic phases were washed with 100 ml of saturated sodium chloride solution, dried over magnesium sulfate and evaporated in a vacuum. The oil obtained was dissolved in 70 ml of anhydrous dimethylformamide, treated with 1.52 g of sodium azide and the reaction mixture was heated to 60° for 15 hours while stirring. After cooling, the solution was poured into 140 ml of water and extracted twice with 140 ml of diethyl ether each time. The combined organic phases were washed once with 100 ml of water and once with 100 ml of saturated sodium chloride solution, dried over magnesium sulfate and the solution was concentrated in a vacuum. The brown oil obtained was purified by column chromatography on silica gel (toluene). 1.9 g (58%) of (R)-1-(2-azido-propyl)-4,5-dihydro-8-methoxy-1H-benz[g]indole were obtained as a light yellow oil.

Quelle