(5RS)-5-hydroxy-5-(2-iodo-3-methoxy-6-pyridyl)-pentanoic acid methyl ester → 5-(2-Iodo-3-methoxy-6-pyridyl)-5-oxopentanoic acid methyl ester

HRID 55279Notes

Reaction equation

HRID 55279 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH2:5][CH2:6][CH:7]([OH:17])[C:8]1[N:13]=[C:12]([I:14])[C:11]([O:15][CH3:16])=[CH:10][CH:9]=1>[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH2:5][CH2:6][C:7]([C:8]1[N:13]=[C:12]([I:14])[C:11]([O:15][CH3:16])=[CH:10][CH:9]=1)=[O:17]

Participants

3

Reactant 1

HCID 54350032(5RS)-5-hydroxy-5-(2-iodo-3-methoxy-6-pyridyl)-pentanoic acid methyl ester

Product 1

HCID 538713035-(2-Iodo-3-methoxy-6-pyridyl)-5-oxopentanoic acid methyl esterYield 43.3%

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

Under the conditions of example 16 E, 9.98 g of (5RS)-5-hydroxy-5-(2-iodo-3-methoxy-6-pyridyl)-pentanoic acid methyl ester is reacted with 43 g of manganese dioxide for 6 hours, worked up, and the crude product is chromatographed on silica gel with hexane/0-35% ethyl acetate. 4.3 g of 5-(2-iodo-3-methoxy-6-pyridyl)-5-oxopentanoic acid methyl ester of melting point 111° C. is obtained.

Workup

  1. customthe crude product is chromatographed on silica gel with hexane/0-35% ethyl acetate

Sources & evidence

ORD record
ord-bb22d03db6854794a05e850718407c3c
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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