Cesium carbonate → (2R)-1-[2-(4-iodophenoxy)ethyl]-2-methylpyrrolidine

HRID 215774

반응식

HRID 215774 반응식
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][NH:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([I:23])=[CH:19][CH:18]=1>C(#N)C>[I:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:15][CH2:14][N:3]2[CH2:4][CH2:5][CH2:6][C@H:2]2[CH3:1])=[CH:18][CH:19]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 641544(R)-2-MethylpyrrolidineHCID 113580261-(2-Chloroethoxy)-4-iodobenzene

생성물 1

HCID 58186897(2R)-1-[2-(4-iodophenoxy)ethyl]-2-methylpyrrolidine수율 78%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
100 °C

실험 절차

To a suspension of (2R)-2-methylpyrrolidine (0.60 g) and cesium carbonate (1.2 g) in acetonitrile (3 mL), 1-(2-chloroethoxy)-4-iodobenzene obtained in Example 60-(1) (0.87 g) was added and the mixture was heated to 100° C., at which it was stirred for 9 hours. The reaction mixture was cooled to room temperature and filtered to remove insoluble materials, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=9:1 to 1:1) to give the titled compound (0.80 g, 78%) as a colorless oil.

후처리

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. customto remove insoluble materials
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=9:1 to 1:1)

출처 및 근거

ORD 기록
ord-3193f116be28418daa74b765fecf8830
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193176B2

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