Methyl morpholine oxide → 1,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-one

HRID 2389900Notes

Reaction equation

HRID 2389900 reaction equation
[CH2:1]1[C:9]2[C:4](=[N:5][CH:6]=[C:7]3[CH2:12][CH2:11][CH:10]([OH:13])[C:8]3=2)[O:3][CH2:2]1.C[N+]1([O-])CCOCC1>C(#N)C>[CH2:1]1[C:9]2[C:4](=[N:5][CH:6]=[C:7]3[CH2:12][CH2:11][C:10](=[O:13])[C:8]3=2)[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxideHCID 591793711,6,7,8-tetrahydro-2H-cyclopenta[d]furo[2,3-b]pyridin-8-ol

Product 1

HCID 591793681,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-oneYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 1,6,7,8-tetrahydro-2H-cyclopenta[d]furo[2,3-b]pyridin-8-ol (500 mg, 2.82 mmol), 4 Å molecular sieves (1 g), 4-methylmorpholine N-oxide (825 mg, 7.05 mmol) and tetra-n-propylammonium perruthenate(VII) (99 mg, 0.282 mmol) in acetonitrile (15 mL) was stirred at room temperature for 15 min. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (335 mg, yield 68%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-f4fb486558a648f39559cb141f8c0017
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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