Tetrapropylammonium → HCID 67482095, compound

HRID 2214080Notes

Reaction equation

HRID 2214080 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][CH2:8][CH:7]1[OH:11].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][CH2:8][C:7]1=[O:11]

Participants

5

Reactant 3

HCID 9559TetrapropylammoniumHCID 82029Methyl morpholine oxideHCID 674821962-(3,4-Dichloro-phenyl)-3-(2-hydroxy-cyclopentyl)-propionic acid methyl ester

Product 1

HCID 67482095HCID 67482095, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2-(3,4-dichloro-phenyl)-3-(2-hydroxy-cyclopentyl)-propionic acid methyl ester (prepared as in Example 25, 408.5 mg, 1.28 mmol), N-methylmorpholine N-oxide (679 mg, 5.79 mmol), and powdered molecular sieves (1.29 g) in methylene chloride (2.6 mL) at 25° C. was treated with tetrapropylammonium perrhuthenate (45 mg, 0.12 mmol). The resulting mixture was stirred at 25° C. for 2 h. 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-(2-oxo-cyclopentyl)-propionic acid methyl ester (278.2 mg, 68.5%) as a clear oil: EI-HRMS m/e calcd for C15H16Cl2O3 (M+) 314.0476, found 314.0476.

Workup

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

Sources & evidence

ORD record
ord-8cdc329dfe7f4912b2c86e553f4b1eeb
Source dataset
uspto-grants-2006_09
Patent number
US07105671B2

Reaction notes

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