Methyl morpholine oxide → 2-(2,3-Dihydroxy-3-methyl-butoxy)-isoindole-1,3-dione

HRID 2218452Notes

Reaction equation

HRID 2218452 reaction equation
CC(C)=C[CH2:4][O:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16].C[N+]1([O-])CC[O:22]CC1.[C:26]([OH:30])([CH3:29])([CH3:28])[CH3:27].C1COCC1.O>S(S([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+]>[OH:22][CH:27]([C:26]([OH:30])([CH3:29])[CH3:28])[CH2:4][O:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16]

Participants

5

Reactant 3

HCID 82029Methyl morpholine oxideHCID 22124471t-Butanol tetrahydrofuran waterHCID 222862302-(3-Methylbut-2-enyloxy)isoindoline-1,3-dione

Product 1

HCID 222864532-(2,3-Dihydroxy-3-methyl-butoxy)-isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 146045Sodium dithionateSolvent

Procedure

2-(3-Methyl-but-2-enyloxy)-isoindole-1,3-dione was dissolved in a t-butanol/THF/H2O solution (10 mL/3 mL/1 mL) and charged with N-methylmorpholine N-oxide (0.085 g, 0.73 mmol) and a catalytic amount of potassium osmate dihydrate. After stirring for 17 hours the reaction was diluted with a saturated solution of sodium metabisulfate and partitioned with ethyl acetate. The organic layer was washed twice with saturated solution of sodium metabisulfate, twice with saturated sodium chloride solution, collected and dried over Na2SO4, filtered and concentrated in vacuo affording 2-(2,3-dihydroxy-3-methyl-butoxy)-isoindole-1,3-dione as a clear oil, which was charged with dichloromethane (10 mL), 2,2-dimethoxypropane (0.12 mL, 0.75 mmol) and a catalytic amount of p-toluenesulfonic acid. After stirring for 17 hours, the reaction was concentrated in vacuo, and partitioned between ethyl acetate and water. The organic layer was washed twice with water, once with saturated sodium chloride solution, collected and dried over Na2SO4, filtered and concentrated in vacuo, affording 2-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-ylmethoxy)-isoindole-1,3-dione as a light brown solid (0.158 g, 77.1%): 1H NMR (400 MHz; DMSO-d6) δ 7.82 s, (4H), 4.12-4.26 (m, 2H), 4.04-4.07 (m, 1H), 1.22 (s, 9H), 1.17 (s, 3H), 0.97 s(3H).

Workup

  1. custompartitioned with ethyl acetate
  2. washThe organic layer was washed twice with saturated solution of sodium metabisulfate, twice with saturated sodium chloride solution
  3. customcollected
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a31a5313ad2d4916aa64f5076df9d3b7
Source dataset
uspto-grants-2008_08
Patent number
US07411001B2

Reaction notes

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