6,7-dihydro-5H-cyclopenta[c]pyridin-3-ylmethanol → 6,7-Dihydro-5H-cyclopenta[c]pyridine-3-carbaldehyde

HRID 1943163Notes

Reaction equation

HRID 1943163 reaction equation
[CH:1]1[C:6]2[CH2:7][CH2:8][CH2:9][C:5]=2[CH:4]=[C:3]([CH2:10][OH:11])[N:2]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH:1]1[C:6]2[CH2:7][CH2:8][CH2:9][C:5]=2[CH:4]=[C:3]([CH:10]=[O:11])[N:2]=1

Participants

4

Reactant 1

HCID 685981886,7-dihydro-5H-cyclopenta[c]pyridin-3-ylmethanol

Product 1

HCID 866420966,7-Dihydro-5H-cyclopenta[c]pyridine-3-carbaldehydeYield 59%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 6,7-dihydro-5H-cyclopenta[c]pyridin-3-ylmethanol (189 mg, 1.267 mmol) in DCM (10 ml) at rt under argon was treated with manganese dioxide (1.101 g, 12.67 mmol) and then stirred at rt for 2 h, filtered through a thin pad of Kieselguhr, eluting with DCM (40 ml), the organic extracts were evaporated to give the crude product as a brown oil (110 mg, 59%).

Workup

  1. filtrationfiltered through a thin pad of Kieselguhr
  2. washeluting with DCM (40 ml)
  3. customthe organic extracts were evaporated

Sources & evidence

ORD record
ord-bfcae35bf4a748bb8a612d5e200ca65a
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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