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

HRID 656595노트

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HRID 656595 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 30318Osmium Tetroxide촉매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9ce1d4a943174516bab3e34c01472781
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071766B2

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