Methanol → (1R,4S)-4-hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid 2-methyl ester

HRID 643831Notes

Reaction equation

HRID 643831 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([OH:10])[CH:7]=[C:6]1[C:11]([O:13]C)=[O:12])=[O:4].[Li+].[OH-].C1(C)C=CC=CC=1.CO>O1CCOCC1.O>[CH3:1][O:2][C:3]([C:5]1[C@H:6]([C:11]([OH:13])=[O:12])[CH2:7][C@H:8]([OH:10])[CH:9]=1)=[O:4]

Participants

7

Reactant 4

HCID 887MethanolHCID 1140TolueneHCID 3939Lithium HydroxideHCID 591654434-Hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid dimethyl ester

Product 1

HCID 68410381(1R,4S)-4-hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid 2-methyl esterYield 27%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To an ice-cold solution of compound 27 (3.4 g, 22 mmol) dissolved in dioxane and water (1:1, 110 mL), LiOH (0.52 g, 22 mmol) was added. After two and a half hours the mixture was co-evaporated with toluene and methanol. Purification by flash chromatography (toluene/Ethyl acetate 3:1+1% HOAc) gave the title compound (1.0 g, 27%) as yellow-white crystals.

Workup

  1. customPurification by flash chromatography (toluene/Ethyl acetate 3:1+1% HOAc)

Sources & evidence

ORD record
ord-f915b318e0fe4668b64f4f222c518eb1
Source dataset
uspto-grants-2010_04
Patent number
US07700552B2

Reaction notes

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