Tetrapropylammonium → 2-(3,4-Dichloro-phenyl)-3-(3-oxo-cyclopentyl)-propionic acid methyl ester

HRID 854829Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:20])[CH:4]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH:8]([OH:11])[CH2:7]1.C[N+]1([O-])CCOCC1.C([N+](CCC)(CCC)CCC)CC>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:20])[CH:4]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][C:8](=[O:11])[CH2:7]1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 2-(3,4-dichloro-phenyl)-3-(3-hydroxy-cyclopentyl)-propionic acid methyl ester (prepared as in Example 36, 356.4 mg, 1.12 mmol), N-methylmorpholine N-oxide (197 mg, 1.68 mmol), and powdered molecular sieves (1.12 g) in methylene chloride (2.25 mL) at 25° C. was treated with tetrapropylammonium perrhuthenate (20 mg, 0.05 mmol). The resulting mixture was stirred at 25° C. for 30 min. At this time, the reaction was filtered through a pad of celite (ethyl acetate as eluent). The filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 75/25 hexanes/ethyl acetate) afforded 2-(3,4-dichloro-phenyl)-3-(3-oxo-cyclopentyl)-propionic acid methyl ester (261.3 mg, 73.8%) as a clear oil: EI-HRMS m/e calcd for C15H16Cl2O3 (M+Na)+ 337.0370. found 337.0371.

Workup

customat 25° C.
filtrationAt this time, the reaction was filtered through a pad of celite (ethyl acetate as eluent)
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-15a79bed1e404d30b1d0eef9aa57ed4e
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259166B2

Reaction notes

Loading…