Sodium Iodide → (2R)-1-[3-(4-iodophenoxy)propyl]-2-methylpyrrolidine

HRID 215759

반응식

HRID 215759 반응식
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][CH:7]=1.[CH3:13][C@@H:14]1[CH2:18][CH2:17][CH2:16][NH:15]1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[I:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:15]2[CH2:16][CH2:17][CH2:18][C@H:14]2[CH3:13])=[CH:7][CH:8]=1

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 641544(R)-2-MethylpyrrolidineHCID 158955201-(3-Chloropropoxy)-4-iodobenzene

생성물 1

HCID 57675747(2R)-1-[3-(4-iodophenoxy)propyl]-2-methylpyrrolidine

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

반응 조건

온도
100 °C

실험 절차

A suspension of 1-(3-chloropropoxy)-4-iodobenzene obtained in Example 1-(1) (2.79 g), (R)-2-methylpyrrolidine (0.961 g), sodium iodide (0.282 g) and potassium carbonate (2.60 g) in acetonitrile (2.8 mL) was stirred in a sealed tube at 100° C. for 5 hours. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=10:1) to give the titled compound (3.27 g) as a yellow oil.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=10:1)

출처 및 근거

ORD 기록
ord-8f4c30c8705148e7a0a39fc309356f2a
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193176B2

연결된 노트

불러오는 중…