HCID 22047127, compound → 2,3-Dihydrofuro[2,3-c]pyridine-5-carboxylic acid

HRID 1072987Notes

Reaction equation

HRID 1072987 reaction equation
Cl[C:2]1[N:3]=[C:4]([C:11]([OH:13])=[O:12])[CH:5]=[C:6]2[CH:10]=[CH:9][O:8][C:7]=12>CO>[O:8]1[C:7]2=[CH:2][N:3]=[C:4]([C:11]([OH:13])=[O:12])[CH:5]=[C:6]2[CH2:10][CH2:9]1

Participants

3

Reactant 1

HCID 22047127HCID 22047127, compound

Product 1

HCID 220469762,3-Dihydrofuro[2,3-c]pyridine-5-carboxylic acidYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

C7 (980 mg, 4.98 mmol) is dissolved in 75 mL MeOH containing 500 mg 20% palladium hydroxide on carbon in a 250 mL Parr shaker bottle. The reaction mixture is hydrogenated at 20 PSI for 24 h. The catalyst is removed by filtration and the filtrate is concentrated in vacuo to a white solid. The solid is dissolved in MeOH and is loaded onto 20 mL Dowex 50W-X2 ion exchange resin (hydrogen form) which had been prewashed with MeOH. The column is eluted with 50 mL MeOH followed by 150 mL 5% TEA in MeOH to afford 2,3-dihydrofuro[2,3-c]pyridine-5-carboxylic acid (C8) (74% yield). HRMS (FAB) calculated for C8H7NO3+H: 166.0504, found 166.0498 (M+H).

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated in vacuo to a white solid
  3. dissolutionThe solid is dissolved in MeOH
  4. washThe column is eluted with 50 mL MeOH

Sources & evidence

ORD record
ord-0988d6a268ad430e931518955a9044a7
Source dataset
uspto-grants-2005_06
Patent number
US06911543B2

Reaction notes

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