2-(3,4-Dichloro-phenyl)-3-[3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-propionic acid methyl ester → 2-(3,4-Dichloro-phenyl)-3-(3-hydroxy-cyclopentyl)-propionic acid methyl ester

HRID 854795Notes

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][CH:8]([O:11]C2CCCCO2)[CH2:7]1>CO>[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][CH:8]([OH:11])[CH2:7]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2-(3,4-dichloro-phenyl)-3-[3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-propionic acid methyl ester (prepared as in Example 35, 1.03 g, 2.57 mmol) in methanol (6.4 mL) was treated with Amberlyst® 15 ion exchange resin (77 mg). The resulting reaction mixture was stirred at 25° C. for 16 h and then was heated at 45° C. for 1 h. The reaction mixture was allowed to cool to 25° C., and the resin was then filtered off and then washed well with ethyl acetate. The filtrate was concentrated in vacuo to afford 2-(3,4-dichloro-phenyl)-3-(3-hydroxy-cyclopentyl)-propionic acid methyl ester (807.7 mg, 99%) as a yellow oil which was used without further purification.

Workup

customThe resulting reaction mixture
temperaturewas heated at 45° C. for 1 h
temperatureto cool to 25° C.
filtrationthe resin was then filtered off
washwashed well with ethyl acetate
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-a16df1d5820540e0b0c2819d7d3a67ec
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259166B2

Reaction notes

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