Methyl morpholine oxide → 2-((3R,4S)-3,4-dihydroxycyclopentyloxy)isoindoline-1,3-dione

HRID 1917494Notes

Reaction equation

HRID 1917494 reaction equation
[CH:1]1([O:6][N:7]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=[O:17])[CH2:5]C=C[CH2:2]1.C[N+]1([O-])CCOCC1.[O:26]1[CH2:31][CH2:30][O:29]CC1.O>O=[Os](=O)(=O)=O>[OH:26][C@H:31]1[C@@H:30]([OH:29])[CH2:2][CH:1]([O:6][N:7]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=[O:17])[CH2:5]1

Participants

5

Reactant 3

HCID 82029Methyl morpholine oxideHCID 197740932-(Cyclopent-3-enyloxy)isoindoline-1,3-dioneHCID 218864351,4-Dioxane--water (1/1)

Product 1

HCID 579990402-((3R,4S)-3,4-dihydroxycyclopentyloxy)isoindoline-1,3-dioneYield 77%

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To a solution of 2-(cyclopent-3-enyloxy)isoindoline-1,3-dione (736 mg, 3.2 mmol) in dioxane —H2O (5.0 mL, 4:1) was added NMO (421 mg, 3.60 mmol) and OsO4 (1.0 mL mg, 0.32 mmol, 2.5 wt % in H2O) and the reaction mixture was stirred for 24 h at rt. Quenched with 10% aqueous Na2S2O3 solution and extracted with ethyl acetate. The combined organic layers washed with brine and dried over anhydrous Na2SO4. Filtered and concentrated to provide yellow oil, which was purified by flash chromatography (80% EtOAc-hexane) to yield 2-((3R,45)-3,4-dihydroxycyclopentyloxy)isoindoline-1,3-dione (650 mg, 77%) as light yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.94-2.12 (m, 2H) 2.14-2.35 (m, 2H) 4.22-4.88 (m, 2H) 4.75-5.11 (m, 1H) 7.67-7.78 (m, 2H) 7.79-7.86 (m, 2H). MS (ES) [M+H] calculated for C13H14NO5, 264.08; found 264.20.

Workup

  1. customQuenched with 10% aqueous Na2S2O3 solution
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationFiltered
  6. concentrationconcentrated
  7. customto provide yellow oil, which
  8. customwas purified by flash chromatography (80% EtOAc-hexane)

Sources & evidence

ORD record
ord-eb55d801342c4bc99c064df225730e7b
Source dataset
uspto-grants-2013_12
Patent number
US08618290B2

Reaction notes

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