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

HRID 656595Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 656595
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 30318Osmium TetroxideKatalysator

Versuchsvorschrift

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,4S)-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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-9ce1d4a943174516bab3e34c01472781
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071766B2

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