Methyl morpholine oxide → HCID 86590314, compound

HRID 899793Notes

Reaction equation

HRID 899793 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][C:14]1([CH2:17][OH:18])[CH2:16][CH2:15]1.C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][C:14]1([CH:17]=[O:18])[CH2:15][CH2:16]1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 69178338HCID 69178338, compound

Product 1

HCID 86590314HCID 86590314, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-cyclopropane-methanol (0.31 g, 1.26 mmol) in CH2Cl2 (6 mL) was added sequentially 3 Å molecular sieves (0.644 g), N-methylmorpholine N-oxide (0.223 g, 1.90 mmol), and tetrapropylammonium perruthenate (88 mg, 0.25 mmol). After 30 minutes, the mixture was filtered through silica gel and the cake was washed with ether. The solvent was removed from the filtrate under reduced pressure and provided 0.25 g (82%) of 1-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-cyclopropanecarboxaldehyde as a colorless oil.

Workup

  1. filtrationthe mixture was filtered through silica gel
  2. washthe cake was washed with ether
  3. customThe solvent was removed from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-b94e64131eb440118f8eae3fb3273064
Source dataset
uspto-grants-2008_04
Patent number
US07354934B2

Reaction notes

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