Reaktion #51977

Reaktionsgleichung

sodium borohydride

2-chloro-1-(1-methyl-1H-pyrrol-2-yl)ethanol

Croce

methylamine

Sodium borohydride

→

title compound

2-(methylamino)-1-(1-methyl-1H-pyrrol-2-yl)ethanol

Lösungsmittel

methanol

methanol

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeSynthesis, 1990, 212-213) (2.05 g)
2. 2
   Temperaturto warm to room temperature
3. 3
   workup.STIRRINGThe reaction mixture is stirred at room temperature for 18 h
4. 4
   Temperaturcooled to 0° C
5. 5
   workup.STIRRINGThe reaction mixture is stirred at 0° C. for 30 min
6. 6
   Temperaturto warm to room temperature
7. 7
   workup.STIRRINGThe reaction mixture is stirred at room temperature for 18 h
8. 8
   workup.STIRRINGthe reaction mixture is stirred at room temperature for 18 h
9. 9
   SonstigeThe reaction is quenched with a 1 N HCl solution
10. 10
    Einengenconcentrated in vacuo
11. 11
    Sonstigeto remove methanol
12. 12
    Extraktionextracted with CH2Cl2 (4×100 mL)
13. 13
    TrocknenThe combined organic layers are dried (MgSO4)
14. 14
    Filtrationfiltered
15. 15
    Einengenconcentrated in vacuo
16. 16
    SonstigeThe resulting yellow oil is crystallized from ethyl acetate

Vorschrift

2-chloro-1-(1-methyl-1H-pyrrol-2-yl)ethanol (Croce, P. D.; Ferraccioli, R.; Ritieni, A. Synthesis, 1990, 212-213) (2.05 g) is dissolved in methanol (40 mL) and added dropwise to a 2.0 M solution of methylamine in methanol (65 mL) at 0° C. The reaction mixture is stirred at 0° C. for 1 h and then allowed to warm to room temperature. The reaction mixture is stirred at room temperature for 18 h and then cooled to 0° C. Sodium borohydride (0.738 g) in H2O (40 mL) is added dropwise. The reaction mixture is stirred at 0° C. for 30 min and then allowed to warm to room temperature. The reaction mixture is stirred at room temperature for 18 h. An additional 0.738 g (19.5 mmol) of sodium borohydride is added and the reaction mixture is stirred at room temperature for 18 h. The reaction is quenched with a 1 N HCl solution and then concentrated in vacuo to remove methanol. The aqueous layer is adjusted to pH 12 with a 2 N NaOH solution and extracted with CH2Cl2 (4×100 mL). The combined organic layers are dried (MgSO4), filtered, and concentrated in vacuo. The resulting yellow oil is crystallized from ethyl acetate to yield 0.772 g of the title compound as a white solid.

Quelle