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Triethylamine → HCID 44819172、化合物

HRID 1909634
ノート
印刷プレビュー

反応式

HRID 1909634 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][CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34].O.ClCCl>ClCCl>[CH3:36][O:35][C:33](=[O:34])[CH2:32][CH2:31][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
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 107604Methyl 4-bromobutyrateHCID 21908982Water methylene chlorideHCID 42641832(R)-2-[4-(4-Chlorophenoxy)phenoxymethyl]pyrrolidine

生成物 1

HCID 44819172HCID 44819172、化合物収率 57%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒

反応条件

温度
30 °C

実験手順

To a solution of Example 18 (step 4) (0.8 g, 2.63 mmol) in dichloromethane (7.6 mL) was added triethylamine (0.78 mL, 5.60 mmol) and methyl 4-bromobutyrate (0.35 mL, 3.04 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 (0.60 g, 57%).

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-5a176c43cd944fc8afffb2b591090fd9
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

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