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

HRID 215759

反応式

HRID 215759 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8f4c30c8705148e7a0a39fc309356f2a
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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