7-(1-methylethylidene)-1,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-one → 7-isopropyl-1,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-one

HRID 2389902Notes

Reaction equation

HRID 2389902 reaction equation
[CH3:1][C:2](=[C:4]1[C:15](=[O:16])[C:7]2=[C:8]3[CH2:14][CH2:13][O:12][C:9]3=[N:10][CH:11]=[C:6]2[CH2:5]1)[CH3:3]>CO.[C].[Pd]>[CH:2]([CH:4]1[C:15](=[O:16])[C:7]2=[C:8]3[CH2:14][CH2:13][O:12][C:9]3=[N:10][CH:11]=[C:6]2[CH2:5]1)([CH3:3])[CH3:1]

Participants

4

Reactant 1

HCID 591794017-(1-methylethylidene)-1,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-one

Product 1

HCID 591793757-isopropyl-1,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-oneYield 85.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 7-(1-methylethylidene)-1,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-one (539 mg, 2.51 mmol) in methanol (20 mL) was added palladium-carbon powder (50 mg), and the mixture was stirred at room temperature for 3 hr under a hydrogen atmosphere. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60) to give the title compound (465 mg, yield 85%).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60)

Sources & evidence

ORD record
ord-53eef3aa24d0433e8529afa3b103ea73
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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