Iodobenzene → 1-Phenylpyrrolidine

HRID 641909

反応式

HRID 641909 の反応式
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.N1CCC[C@H]1C(O)=O.I[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>[Cu]I.CS(C)=O>[C:15]1([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

6

反応物 3

HCID 11575IodobenzeneHCID 31268PyrrolidineHCID 145742L-Proline

生成物 1

HCID 777261-Phenylpyrrolidine収率 59.6%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
60 °C

実験手順

Pyrrolidine (21.6 g, 304.23 mmol), L-proline (1.12 g, 9.74 mmol), and CuI (960 mg, 5.05 mmol) were added sequentially to 1-iodobenzene (10.0 g, 49.02 mmol). DMSO (40 mL) was then added, and the resulting solution was stirred at 60° C. for 20 hours. The reaction mixture was then quenched by adding 400 mL of iced water. The resulting solution was extracted with ethyl acetate (3×150 mL), and the organic layers were combined, dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography using a 1:100 ethyl acetate/petroleum ether solvent system to afford 4.3 g (57%) of 1-phenylpyrrolidine as brown oil.

後処理

  1. customThe reaction mixture was then quenched
  2. additionby adding 400 mL of iced water
  3. extractionThe resulting solution was extracted with ethyl acetate (3×150 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-a24edf014d2a41488f03db31dc34e41c
出典データセット
uspto-grants-2010_04
特許番号
US07696229B2

関連ノート

読み込み中…