1-[3-(Benzyloxy)propyl]-5-methoxy-1,3-dihydro-2h-pyrrolo[3,2-b]pyridin-2-one → 1-(3-Hydroxypropyl)-5-methoxy-1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one

HRID 1767563Notes

Reaction equation

HRID 1767563 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:20]2[C:15](=[N:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[CH2:14][C:13]1=[O:23])C1C=CC=CC=1>CO.[Pd]>[OH:8][CH2:9][CH2:10][CH2:11][N:12]1[C:20]2[C:15](=[N:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[CH2:14][C:13]1=[O:23]

Participants

4

Reactant 1

HCID 120351231-[3-(Benzyloxy)propyl]-5-methoxy-1,3-dihydro-2h-pyrrolo[3,2-b]pyridin-2-one

Product 1

HCID 113904261-(3-Hydroxypropyl)-5-methoxy-1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under a hydrogen pressure of 45 psi, 510 mg (1.63 mmol) of the compound obtained in Step C and 72 mg of palladium-on-carbon suspended in 10 ml of methanol are stirred for 15 hours at room temperature. After filtration over Celite and evaporation, the residue is hydrolysed with water and then extracted with ethyl acetate. The organic phase is dried over magnesium sulphate and evaporated to yield the title compound in the form of a brown solid.

Workup

  1. filtrationAfter filtration
  2. customover Celite and evaporation
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-9adf6bf41cf04bddb3cba8f2a03fe590
Source dataset
uspto-grants-2007_06
Patent number
US07235550B2

Reaction notes

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