반응 #45898

반응 방정식

sodium iodide

dimethylamine hydrochloride

potassium carbonate

methanesulfonyl chloride

triethylamine

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

→

compound

수율 4.1%

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

수율 4.1%

용매

acetone

dimethylformamide

dichloromethane

반응 조건

후처리

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

실험 절차

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.

출처