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

HRID 215776

反応式

HRID 215776 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][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([I:25])=[CH:21][CH:20]=1>C(#N)C>[I:25][C:22]1[CH:23]=[CH:24][C:19]([O:18][CH2:17][CH2:16][CH2:15][CH2:14][N:3]2[CH2:4][CH2:5][CH2:6][C@H:2]2[CH3:1])=[CH:20][CH:21]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 641544(R)-2-MethylpyrrolidineHCID 581868981-(4-Chlorobutoxy)-4-iodobenzene

生成物 1

HCID 58186896(2R)-1-[4-(4-iodophenoxy)butyl]-2-methylpyrrolidine収率 89%

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 (0.8 g) and cesium carbonate (1.7 g) in acetonitrile (5 mL), 1-(4-chlorobutoxy)-4-iodobenzene obtained in Example 61-(1) (1.4 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 (1.4 g, 89%) 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-2a14b215c4e9446ea8584fe8207de3a1
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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