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

HRID 17620

반응식

HRID 17620 반응식
CS(Cl)(=O)=O.[CH2:6]([N:8](CC)[CH2:9]C)C.O[CH2:14][C@@H:15]1[CH2:19][CH2:18][CH2:17][N:16]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].[I-].[Na+].Cl.CNC.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C)C=O.ClCCl>[CH3:6][N:8]([CH2:14][C@@H:15]1[CH2:19][CH2:18][CH2:17][N:16]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH3:9]

참가 물질

10

반응물 6

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 643448(S)-(-)-N-Boc-prolinol

생성물 1

HCID 60017963tert-Butyl (2S)-2-[(dimethylamino)methyl]pyrrolidine-1-carboxylate수율 4.1%

시약·촉매·용매 3

HCID 180Acetone용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

반응 조건

온도
85 °C

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.

후처리

  1. temperaturewith cooling with ice
  2. customThe reaction liquid
  3. concentrationwas concentrated under reduced pressure
  4. dissolutiondissolved in ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialAfter drying over anhydrous sodium sulfate
  7. customthe insoluble matter was separated by filtration
  8. customthe residue obtained by concentration
  9. temperatureby heating
  10. customThe reaction liquid
  11. concentrationwas concentrated under reduced pressure
  12. washwashed with water and saturated brine
  13. dry with materialAfter drying over anhydrous sodium sulfate
  14. customthe insoluble matter was separated by filtration
  15. customthe residue obtained by concentration
  16. stirringby stirring at room temperature for 24 hours
  17. customThe reaction liquid
  18. concentrationwas concentrated under reduced pressure
  19. washwashed with water and saturated brine
  20. dry with materialAfter drying over anhydrous sodium sulfate and concentration
  21. customthe resulting residue was purified by silica gel column chromatography (eluent, chloroform

출처 및 근거

ORD 기록
ord-e4e4f29845684645b77ddb16ddff058f
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

연결된 노트

불러오는 중…