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

HRID 1662520Notes

Reaction equation

[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

Participants

Conditions

Temperature: 40 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-dbe411cac0f2463da9e0a49b5b6fd302
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030354B2

Reaction notes

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