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

HRID 215774

反応式

HRID 215774 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3193f116be28418daa74b765fecf8830
出典データセット
uspto-grants-2012_06
特許番号
US08193176B2

関連ノート

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