Water → 3-Cyclopropyl-3-(3-hydroxyphenyl)propanoic acid

HRID 1662520ノート

反応式

HRID 1662520 の反応式
[O:1]1[CH2:6][CH2:5]OCC1.[OH2:7].[OH2:8].[NH2:9][C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[CH:14][CH:15]=1.[C:19]([O:25][CH3:26])(=[O:24])/[CH:20]=[CH:21]/[CH2:22][CH3:23]>CCOC(C)=O>[NH2:9][C:10]1[CH:11]=[C:12]([C@H:21]([CH2:22][CH3:23])[CH2:20][C:19]([O:25][CH3:26])=[O:24])[CH:13]=[CH:14][CH:15]=1.[CH:22]1([CH:23]([C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([OH:8])[CH:11]=2)[CH2:5][C:6]([OH:1])=[O:7])[CH2:20][CH2:21]1

参加物

7

反応物 4

HCID 962WaterHCID 312751,4-DioxaneHCID 5364718Methyl 2-pentenoateHCID 143894233-Aminophenylboronic acid monohydrate

生成物 2

HCID 577059733-Cyclopropyl-3-(3-hydroxyphenyl)propanoic acid収率 44.1%HCID 57707126(R)-methyl 3-(3-aminophenyl)pentanoate

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
40 °C

実験手順

A mixture of dioxane and water (10/1 dioxane/water, 22 mL) was added to a flask charged with hydroxyl[(S)-Binap]-rhodium(I) dimer (260 mg, 175 μmol), and 3-aminophenylboronic acid hydrate (81.1) (available from Aldrich) (3.394 g, 21902 μmol) and flushed with nitrogen and (E)-methyl pent-2-enoate (81.2) (available from Acros) (0.500 g, 4380 μmol). The resulting mixture was then stirred at 40° C. overnight. The reaction was diluted with EtOAc and washed with saturated sodium bicarbonate and brine, and then dried over sodium sulfate, filtered, and concentrated. The crude was purified by combiflash chromatography (0 to 20% EtOAc/Hexanes) to provide (R)-methyl 3-(3-aminophenyl)pentanoate or (S)-methyl 3-(3-aminophenyl)pentanoate (8.3) (400 mg, 44.1% yield). The product is believed to be the R enantiomer.

後処理

  1. additionwas added to a flask
  2. washwashed with saturated sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was purified by combiflash chromatography (0 to 20% EtOAc/Hexanes)

出典と根拠

ORDレコード
ord-dbe411cac0f2463da9e0a49b5b6fd302
出典データセット
uspto-grants-2011_10
特許番号
US08030354B2

反応ノート

読み込み中…