HCID 71087871, compound → HCID 71087926, compound

HRID 632122Notes

Reaction equation

HRID 632122 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:12][O:13][CH2:14][CH:15]=2)=[CH:7][N:6]=1)=[O:4].[CH3:16][O:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[O:27][CH2:28][CH2:29][CH:30]=2)=[CH:22][N:21]=1)=[O:19]>CO.[Pd]>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:15][CH2:14][O:13][CH2:12]2)=[CH:7][N:6]=1)=[O:4].[CH3:16][O:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([CH:26]2[CH2:30][CH2:29][CH2:28][O:27]2)=[CH:22][N:21]=1)=[O:19]

Participants

6

Reactant 2

HCID 71087871HCID 71087871, compoundHCID 71087971HCID 71087971, compound

Product 2

HCID 71087700HCID 71087700, compoundHCID 71087926HCID 71087926, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-(2,5-dihydrofuran-3-yl)-pyridine-2-carboxylic acid methyl ester (a1) and 5-(4,5-dihydrofuran-2-yl)-pyridine-2-carboxylic acid methyl ester (a2) (mixture from Example 101 a, 8 g, 39 mmol) in methanol (200 ml) was added palladium on carbon (10% w/w, 0.8 g). The mixture was stirred under hydrogen balloon overnight at room temperature. After concentration, the crude product was purified by column chromatography (silica gel, 100 g, eluting with 30% ethyl acetate in petroleum ether) to give 5-(tetrahydrofuran-3-yl)-pyridine-2-carboxylic acid methyl ester (b1) and 5-(tetrahydrofuran-2-yl)-pyridine-2-carboxylic acid methyl ester (b2) (mixture, b1/b2=1/0.85 at UV 254 nm, 7.8 g, 97%) as colorless oil; MS (EI): m/e=208.1 [M+H]+.

Workup

  1. concentrationAfter concentration
  2. customthe crude product was purified by column chromatography (silica gel, 100 g, eluting with 30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-dbf4dbe604f0424e9f69caff668d16a4
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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