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Diisopropylethylamine → (S)-7-[3-[[(2,3-Dihydro-7-hydroxy-1,4-benzodioxin-2-yl)methyl]amino]propoxy]-2H-1-benzopyran-2-one

HRID 374226
ノート
印刷プレビュー

反応式

HRID 374226 の反応式
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C@H:8]([CH2:11][NH2:12])[O:7][C:6]=2[CH:13]=1.Br[CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:28]=[C:27]2[C:22]([CH:23]=[CH:24][C:25](=[O:29])[O:26]2)=[CH:21][CH:20]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C@H:8]([CH2:11][NH:12][CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:20]=[CH:21][C:22]4[CH:23]=[CH:24][C:25](=[O:29])[O:26][C:27]=4[CH:28]=3)[O:7][C:6]=2[CH:13]=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

5

反応物 3

HCID 81531DiisopropylethylamineHCID 27571767-(3-bromopropoxy)-2H-chromen-2-oneHCID 22844790(S)-2,3-Dihydro-7-hydroxy-1,4-benzodioxin-2-methanamine

生成物 1

HCID 53802521(S)-7-[3-[[(2,3-Dihydro-7-hydroxy-1,4-benzodioxin-2-yl)methyl]amino]propoxy]-2H-1-benzopyran-2-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
86 °C

実験手順

(S)-2,3-Dihydro-7-hydroxy-1,4-benzodioxin-2-methanamine (3.53 g, 16.2 mmole), 7-(3-bromopropoxy)coumarin (4.17 g, 14.7 mmole), and diisopropylethylamine (5.00 ml, 28.7 mmole) were combined in 300 ml of DMF and heated at 86° C. for 24 hours under a nitrogen atmosphere. The solvent was then removed in vacuum and replaced with dichloromethane. The mixture was washed with an equal volume of saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was column chromatographed on 300 g of silica gel using first 75% ethyl acetate/dichloromethane and then 2% methanol/dichloromethane as eluant. The product-containing fractions were concentrated in vacuum and the free base redissolved in warm methanol. Five ml of 4N isopropanolic HCl was added, the mixture was brought to a boil on a hot plate and the solvent gradually replaced with isopropanol. Upon cooling, 2.24 g of the title compound precipitated as an white solid, monohydrochloride, m.p. 245°-248° C.

後処理

  1. customThe solvent was then removed in vacuum
  2. washThe mixture was washed with an equal volume of saturated aqueous sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customchromatographed on 300 g of silica gel using first 75% ethyl acetate/dichloromethane
  7. concentrationThe product-containing fractions were concentrated in vacuum
  8. dissolutionthe free base redissolved in warm methanol
  9. additionFive ml of 4N isopropanolic HCl was added
  10. temperatureUpon cooling
  11. custom2.24 g of the title compound precipitated as an white solid, monohydrochloride, m.p. 245°-248° C.

出典と根拠

ORDレコード
ord-00472e70b7ff4bdd848a408128c02df9
出典データセット
uspto-grants-1992_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05166367

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート