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

HRID 1662520노트

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HRID 1662520 반응식
[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

참가 물질

7

반응물 4

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

생성물 2

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
40 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-dbe411cac0f2463da9e0a49b5b6fd302
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030354B2

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