Methyl morpholine oxide → HCID 69205140, compound

HRID 899799Notes

Reaction equation

HRID 899799 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH:7]([OH:20])[CH2:8][N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19])(=[O:3])[CH3:2].C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[C:1]([O:4][CH2:5][CH2:6][C:7](=[O:20])[CH2:8][N:9]1[C:10](=[O:19])[C:11]2=[CH:18][CH:17]=[CH:16][CH:15]=[C:12]2[C:13]1=[O:14])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 69156663HCID 69156663, compound

Product 1

HCID 69205140HCID 69205140, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of N-(4-acetoxy-2-hydroxybutyl)phthalimide (10.2 g, 36.8 mmol) in CH2Cl2 (185 mL) at 0° C. was treated with molecular seives (18.4 g), N-methylmorpholine oxide (6.46 g, 55.2 mmol), and tetrapropylammonium perruthenate (1.29 g, 3.7 mmol). The mixture was allowed to warm to room temperature over 20 minutes and immediately filtered through silica (using 500 g SiO2 in a coarse glass fritted funnel). The silica was washed with excess diethyl ether (2 L) and concentrated under reduced pressure to afford the desired N-(4-acetoxy-2-oxobutyl)phthalimide (9.22 g, 92%).

Workup

  1. filtrationimmediately filtered through silica (
  2. washThe silica was washed with excess diethyl ether (2 L)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0e590fee93fd48f0a70773c192ac9e68
Source dataset
uspto-grants-2008_04
Patent number
US07354934B2

Reaction notes

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