Triethylamine → HCID 53751739, compound

HRID 1953930Notes

Reaction equation

HRID 1953930 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[C@H:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[O:9][CH:8]([C:16]2[CH:21]=[CH:20][C:19]([O:22]CC3C=CC=CC=3)=[CH:18][CH:17]=2)[O:7]1)=[O:5])[CH3:2].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(O)C.[C].[Pd]>[CH2:14]([O:13][C:11]([C@H:10]1[C@H:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[O:7][CH:8]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)[O:9]1)=[O:12])[CH3:15]

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 54392027HCID 54392027, compound

Product 1

HCID 53751739HCID 53751739, compoundYield 97.7%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A solution of 7.4 g (4R,5R)-2-(4-benzyloxyphenyl)-1,3-dioxolane-4,5-dicarboxylic acid diethyl ester and 0.8 ml of triethylamine in 120 ml of toluene and 40 ml of ethanol was hydrogenated overnight with 1.1 g of 5% palladium carbon at room temperature and normal pressure. After filtration and evaporation of solvent, 5.60 g of (4R,5R)-2-(4-hydroxyphenyl)-1,3-dioxolane-4,5-dicarboxylic acid diethyl ester was obtained.

Workup

  1. filtrationAfter filtration and evaporation of solvent

Sources & evidence

ORD record
ord-29919ae899c84dd6b9209e46369a35fc
Source dataset
uspto-grants-2000_09
Patent number
US06120859

Reaction notes

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