Reaktion #93345

Reaktionsgleichung

n-hexyl bromide

triethylamine

CS2

(3S)-3-Hydroxymethyl-1,2,3,4-tetrahydro-β-carboline

→

title compound

Ausbeute 73.2%

n-Hexyl (3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-β-carboline-2-carbodithioate

Ausbeute 73.2%

Lösungsmittel

dimethylsulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture is stirred at room temperature for 2.5 hours
2. 2
   workup.ADDITIONThe reaction mixture is poured onto ice-water
3. 3
   Extraktionthe mixture is extracted with ethyl acetate
4. 4
   WaschenThe ethyl acetate layer is washed with water
5. 5
   Trocknendried over sodium sulfate
6. 6
   workup.DISTILLATIONdistilled
7. 7
   Sonstigeto remove the solvent
8. 8
   SonstigeThe residue is recrystallized from ether-n-hexane

Vorschrift

(3S)-3-Hydroxymethyl-1,2,3,4-tetrahydro-β-carboline (2.02 g) is dissolved in dimethylsulfoxide (10 ml), and thereto are added triethylamine (1.67 ml) and CS2 (0.72 ml), and the mixture is stirred at room temperature for 20 minutes. To the reaction mixture is added dropwise n-hexyl bromide (1.98 g), and the mixture is stirred at room temperature for 2.5 hours. The reaction mixture is poured onto ice-water and the mixture is extracted with ethyl acetate. The ethyl acetate layer is washed with water, dried over sodium sulfate, and then distilled to remove the solvent. The residue is recrystallized from ether-n-hexane to give the title compound (2.65 g, 73.2%) as colorless needles, m.p. 102°-106° C. NMR (CDCl3, δ): 0.90 (broad, t, 3H, --(CH2)5 --CH3); Mass m/e: 362 (M+), 244 (M+ --C6H13SH); [α]D20 +130.0° (c=1.0, methanol).

Quelle