Reaktion #45898

Reaktionsgleichung

sodium iodide

dimethylamine hydrochloride

potassium carbonate

methanesulfonyl chloride

triethylamine

tert-butyl (2S)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

→

compound

Ausbeute 4.1%

tert-Butyl (2S)-2-[(dimethylamino)methyl]pyrrolidine-1-carboxylate

Ausbeute 4.1%

Lösungsmittel

acetone

dimethylformamide

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwith cooling with ice
2. 2
   SonstigeThe reaction liquid
3. 3
   Einengenwas concentrated under reduced pressure
4. 4
   workup.DISSOLUTIONdissolved in ethyl acetate
5. 5
   Waschenwashed with saturated brine
6. 6
   TrocknenAfter drying over anhydrous sodium sulfate
7. 7
   Sonstigethe insoluble matter was separated by filtration
8. 8
   Sonstigethe residue obtained by concentration
9. 9
   Temperaturby heating
10. 10
    SonstigeThe reaction liquid
11. 11
    Einengenwas concentrated under reduced pressure
12. 12
    Waschenwashed with water and saturated brine
13. 13
    TrocknenAfter drying over anhydrous sodium sulfate
14. 14
    Sonstigethe insoluble matter was separated by filtration
15. 15
    Sonstigethe residue obtained by concentration
16. 16
    workup.STIRRINGby stirring at room temperature for 24 hours
17. 17
    SonstigeThe reaction liquid
18. 18
    Einengenwas concentrated under reduced pressure
19. 19
    Waschenwashed with water and saturated brine
20. 20
    TrocknenAfter drying over anhydrous sodium sulfate and concentration
21. 21
    Sonstigethe resulting residue was purified by silica gel column chromatography (eluent, chloroform

Vorschrift

With cooling with ice, methanesulfonyl chloride (923 μl, 11.9 mmol) and triethylamine (1.94 ml, 13.9 mmol) were added to a dichloromethane (100 ml) solution of tert-butyl (2S)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (2.00 g, 9.94 mmol), followed by stirring for 30 minutes with cooling with ice. The reaction liquid was concentrated under reduced pressure, dissolved in ethyl acetate, and washed with saturated brine. After drying over anhydrous sodium sulfate, the insoluble matter was separated by filtration, and the residue obtained by concentration was dissolved in acetone (50 ml), then sodium iodide (1.49 g, 9.94 mmol) was added, followed by heating under reflux in an oil bath at 85° C. for 5 hours. The reaction liquid was concentrated under reduced pressure, the residue was suspended in ethyl acetate, washed with water and saturated brine. After drying over anhydrous sodium sulfate, the insoluble matter was separated by filtration, the residue obtained by concentration was dissolved in dimethylformamide (30 ml), then dimethylamine hydrochloride (2.43 g, 29.8 mmol) and potassium carbonate (2.75 g, 19.9 mmol) were added, followed by stirring at room temperature for 24 hours. The reaction liquid was concentrated under reduced pressure, the residue was suspended in ethyl acetate, and washed with water and saturated brine. After drying over anhydrous sodium sulfate and concentration, the resulting residue was purified by silica gel column chromatography (eluent, chloroform:methanol=10:1, v/v) to obtain the entitled compound (92.0 mg, 4%) as a colorless oily substance.

Quelle