5-Cyclopentenyl-6-(cyclopropylmethoxy)-pyridine-2-carboxylic acid → 5-Cyclopentyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid

HRID 927418Notes

Reaction equation

HRID 927418 reaction equation
[C:1]1([C:6]2[CH:7]=[CH:8][C:9]([C:17]([OH:19])=[O:18])=[N:10][C:11]=2[O:12][CH2:13][CH:14]2[CH2:16][CH2:15]2)[CH2:5][CH2:4][CH2:3][CH:2]=1.[H][H]>C(O)C.[Pd]>[CH:1]1([C:6]2[CH:7]=[CH:8][C:9]([C:17]([OH:19])=[O:18])=[N:10][C:11]=2[O:12][CH2:13][CH:14]2[CH2:15][CH2:16]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 710874455-Cyclopentenyl-6-(cyclopropylmethoxy)-pyridine-2-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 710875595-Cyclopentyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acidYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The mixture of 5-cyclopentenyl-6-(cyclopropylmethoxy)-pyridine-2-carboxylic acid (0.95 g, 4 mmol), Pd/C (10% w/w, 0.2 g) in 30 mL of ethanol in a hydrogen atmosphere was stirred for 4 h at room temperature. The mixture was filtered and the filtrate was evaporated to dryness to obtain the product (0.76 g, 79%) as white solid. The product was directly used for the next step; MS (LC/MS): 262.1 [M+H]+.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-3579b185cdb64cc6984e4c92859770a1
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

Loading…