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Triethylamine → HCID 68999682、化合物

HRID 1909630
ノート
印刷プレビュー

反応式

HRID 1909630 の反応式
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:19]=[CH:18][C:10]([O:11][CH2:12][C@H:13]3[CH2:17][CH2:16][CH2:15][NH:14]3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32].O.ClCCl>ClCCl>[C:34]([O:33][C:31](=[O:32])[CH2:30][N:14]1[CH2:15][CH2:16][CH2:17][C@@H:13]1[CH2:12][O:11][C:10]1[CH:18]=[CH:19][C:7]([O:6][C:5]2[CH:20]=[CH:21][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:8][CH:9]=1)([CH3:37])([CH3:36])[CH3:35]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8471TriethylamineHCID 79177tert-Butyl bromoacetateHCID 21908982Water methylene chlorideHCID 42641832(R)-2-[4-(4-Chlorophenoxy)phenoxymethyl]pyrrolidine

生成物 1

HCID 68999682HCID 68999682、化合物収率 75.5%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

反応条件

温度
30 °C

実験手順

To a solution of the product from step 4 (0.8 g, 2.63 mmol) in dichloromethane (7.6 mL) was added triethylamine (0.78 mL, 5.60 mmol) and t-butyl bromoacetate (0.45 mL, 3.05 mmol). The resulting solution was stirred at 30° C. overnight. The reaction mixture was poured into water/dichloromethane (50 mL/50 mL). The crude residue was extracted into dichloromethane. The organic portion was washed with water (50 mL), washed with brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by silica gel flash chromatography using hexane/EtOAc (gradient system) to give the title compound (0.83 g, 75%);

後処理

  1. extractionThe crude residue was extracted into dichloromethane
  2. washThe organic portion was washed with water (50 mL)
  3. washwashed with brine (50 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel flash chromatography

出典と根拠

ORDレコード
ord-e25dafca36594e0d9e36649ebbe27b7e
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08598359B2

反応ノート

読み込み中…

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