Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 2-(3,4-Dichloro-phenyl)-3-(2-hydroxy-cyclopentyl)-propionic acid methyl ester

HRID 2214066Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:26])[CH:4]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[O:11]C1CCCCO1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[CH3:1][O:2][C:3](=[O:26])[CH:4]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[OH:11]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2-(3,4-dichloro-phenyl)-3-[2-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-propionic acid methyl ester (prepared as in Example 24, 2.3 g, 5.73 mmol) in ethanol (57.3 mL) at 25° C. was treated with pyridinium p-toluenesulfonate (144 mg, 0.57 mmol). The resulting solution was heated under reflux for 18 h. At this time, the reaction was cooled to 25° C. and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 50/50 hexanes/ethyl acetate) afforded 2-(3,4-dichloro-phenyl)-3-(2-hydroxy-cyclopentyl)-propionic acid methyl ester (1.84 g, 100%) as a clear oil: EI-HRMS m/e calcd for C15H18Cl2O3 (M+Na)+ 339.0527, found 339.0528.

Workup

temperatureThe resulting solution was heated
temperatureunder reflux for 18 h
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-3e89885800fe4f2f8f529468cb4c9c56
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105671B2

Reaction notes

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