Methyl morpholine oxide → HCID 57420146, compound

HRID 1172836Notes

Reaction equation

HRID 1172836 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[N:12]=[C:11]([CH2:13][CH2:14][CH3:15])[C:10]([CH2:16][OH:17])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1>ClCCl.C(OCC)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([CH:16]=[O:17])=[C:11]([CH2:13][CH2:14][CH3:15])[N:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 82029Methyl morpholine oxideHCID 57420145HCID 57420145, compound

Product 1

HCID 57420146HCID 57420146, compound

Reagents, catalysts & solvents 3

HCID 178419074HCID 178419074, compoundCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of the product from Step 4 (30.5 g, 110 mmol), N-methylmorpholine-N-oxide (19.3 g, 165 mmol), tetrapropylammonium perruthenate (1.9 g, 5.5 mmol) and 4 Å molecular sieves (55 g) in dichloromethane (500 mL) was cooled with a water bath at 20° C. and stirred for 1 h. The reaction mixture was diluted with diethyl ether (1.5 L), stirred for 15 min and filtered through a short path of silica gel. Removal of the solvent gave the title product as a light yellow oil.

Workup

  1. stirringstirred for 15 min
  2. filtrationfiltered through a short path of silica gel
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-6a904a77d365472baa1dd93b500a07ee
Source dataset
uspto-grants-2010_11
Patent number
US07834036B2

Reaction notes

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