Isopropanol → trans-2-(2-methyl-2H-indazol-4-yl)cyclopropanecarbaldehyde

HRID 1639753Notes

Reaction equation

HRID 1639753 reaction equation
[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][CH:7]=[C:8]2[C@@H:11]2[CH2:13][C@H:12]2[CH2:14][OH:15])=[N:3]1.C[N+]1([O-])CCOCC1.CC(O)C>C(#N)C>[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][CH:7]=[C:8]2[C@@H:11]2[CH2:13][C@H:12]2[CH:14]=[O:15])=[N:3]1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 82029Methyl morpholine oxideHCID 66720579Trans-[2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methanol

Product 1

HCID 86641920trans-2-(2-methyl-2H-indazol-4-yl)cyclopropanecarbaldehydeYield 77.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trans-[2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methanol (500 mg, 2.47 mmol), 4 Å molecular sieves (200 mg), 4-methylmorpholine N-oxide (724 mg, 6.18 mmol) and tetra-n-propylammonium perruthenate(VII) (43.6 mg, 0.124 mmol) were dissolved in acetonitrile (25 mL), and the mixture was stirred at room temperature for 2 hr. 2-Propanol was added, and the mixture was stirred for 30 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 (382 mg, yield 77%).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-3b837a79616a4d679ac4944abbfdfdda
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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