5-[3-Hydroxy-2-(2-methoxycarbonylethyl)-6-pyridyl]-4-pentynoic acid methyl ester → 5-[3-Hydroxy-2-(2-methoxycarbonylethyl)-6-pyridyl]-pentanoic acid methyl ester

HRID 55311Notes

Reaction equation

HRID 55311 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][C:6]#[C:7][C:8]1[N:13]=[C:12]([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:11]([OH:20])=[CH:10][CH:9]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[N:13]=[C:12]([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:11]([OH:20])=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 542841715-[3-Hydroxy-2-(2-methoxycarbonylethyl)-6-pyridyl]-4-pentynoic acid methyl ester

Product 1

HCID 541155615-[3-Hydroxy-2-(2-methoxycarbonylethyl)-6-pyridyl]-pentanoic acid methyl esterYield 65.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under the conditions of example 14 A, a solution of 1 g of 5-[3-hydroxy-2-(2-methoxycarbonylethyl)-6-pyridyl]-4-pentynoic acid methyl ester in 10 ml of methanol is hydrogenated in the presence of 100 mg of 10% palladium catalyst on activated carbon and worked up. The crude product is chromatographed on silica gel with hexane/0-50% ethyl acetate. 665 mg of 5-[3-hydroxy-2-(2-methoxycarbonylethyl)-6-pyridyl]-pentanoic acid methyl ester of melting point 92°-95° C. is obtained.

Workup

  1. customThe crude product is chromatographed on silica gel with hexane/0-50% ethyl acetate

Sources & evidence

ORD record
ord-1abc353a551f4ffd97ac0d72878e2a35
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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