Methyl morpholine oxide → HCID 66927598, 화합물

HRID 929750노트

반응식

HRID 929750 반응식
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=1)[O:8]2.C[N+]1([O-])CC[O:29]CC1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O=[Os](=O)(=O)=O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[CH2:5][C:6](=[O:29])[CH:7]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=1)[O:8]2

참가 물질

6

반응물 3

HCID 82029Methyl morpholine oxideHCID 656671Sodium PyrosulfiteHCID 23270450HCID 23270450, 화합물

생성물 1

HCID 66927598HCID 66927598, 화합물수율 30%

시약·촉매·용매 2

HCID 30318Osmium Tetroxide촉매HCID 8028Tetrahydrofuran용매

실험 절차

(2R)-3-[(2R,3S)-5,7,3′,4′-tetrakis(methyloxy)-3-hydroxyflavan)]-5,7,3′,4′-tetramethoxyflavan-3-ene (6) (20 mg, 0.030 mmol) was dissolved in THF (5 mL) and OsO4 (0.9 mg, 0.004 mmol) and N-methylmorpholine-N-oxide (16.3 mg, 0.139 mmol) was added. The reaction mixture is stirred 1-2 days at r.t. under argon (TLC monitoring of consumption of starting material). Solution of sodium metabisulfite (10% aq.) was added and reaction mixture was stirred for 30 minutes. Then was made the extraction 3× with dichloromethane, washed with NaHCO3 (sat. aq.), NaCl (sat. aq.) and dried over MgSO4. Evaporation left crude material which was purified on preparative TLC plates (toluene acetone 6:4) to afford (2S,3S)-3-[(2R,3S)-5,7,3′,4′-tetrakis(methyloxy)-3-hydroxyflavan)]-5,7,3′,4′-tetramethoxyflavan-3-one (7) (Rf 0.19, 6 mg, 0.009 mmol, 30%).

후처리

  1. customreaction mixture
  2. stirringwas stirred for 30 minutes
  3. extractionthe extraction 3× with dichloromethane
  4. washwashed with NaHCO3 (sat. aq.), NaCl (sat. aq.)
  5. dry with materialdried over MgSO4
  6. customEvaporation
  7. waitleft crude material which
  8. customwas purified on preparative TLC plates (toluene acetone 6:4)

출처 및 근거

ORD 기록
ord-b675b05df0cb4c528318d8a8d04dcf15
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296717B2

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