Methyl morpholine oxide → HCID 66927598、化合物

HRID 929750ノート

反応式

HRID 929750 の反応式
[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

参加物

6

反応物 3

HCID 82029Methyl morpholine oxideHCID 656671Sodium PyrosulfiteHCID 23270450HCID 23270450、化合物

生成物 1

HCID 66927598HCID 66927598、化合物収率 30%

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

(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%).

後処理

  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)

出典と根拠

ORDレコード
ord-b675b05df0cb4c528318d8a8d04dcf15
出典データセット
uspto-grants-2016_03
特許番号
US09296717B2

反応ノート

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