Triacetoxyperiodinane → HCID 21914148、化合物

HRID 1246193ノート

反応式

HRID 1246193 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH2:24][CH:25]1[CH2:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:26]1[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35]>C(Cl)Cl>[CH:24]([CH:25]1[CH2:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:26]1[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[O:23]

参加物

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 2794669tert-Butyl 2-(hydroxymethyl)-2,3-dihydro-1H-indole-1-carboxylate

生成物 1

HCID 21914148HCID 21914148、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Dess-Martin Reagent (0.011 mol) was added neat over 1 minutes to intermediate (11) (0.010 mol) dissolved in DCM (35 ml). After 15 minutes, the ice bath was removed, and the mixture was allowed to warm to room temperature. More Dess-Martin Reagent (0.33 g) was added, and the mixture was stirred for 30 minutes more. The mixture was re-cooled to 0° C. and treated slowly with a partial suspension/solution of Na2S2O3 (25 g) which had attempted to dissolve in a saturated aqueous NaHCO3 (100 ml) solution. After 10 minutes, the mixture was removed from ice, and the layers were separated. More DCM was added, and the mixture was filtered. The organic was separated from the filtrate, and the combined organic phases were dried, filtered, concentrated and purified through flash column chromatography (eluent: 10% ethyl acetate: hexane, dissolving the sample in 3:1 ethyl acetate: hexane (5 ml)), yielding 1,1-dimethylethyl 2-formyl-2,3-dihydro-1H-indole-1-carboxylate (intermediate 12, mp. 85–87° C.).

後処理

  1. customthe ice bath was removed
  2. additionMore Dess-Martin Reagent (0.33 g) was added
  3. temperatureThe mixture was re-cooled to 0° C.
  4. additiontreated slowly with a partial suspension/solution of Na2S2O3 (25 g) which
  5. dissolutionto dissolve in a saturated aqueous NaHCO3 (100 ml) solution
  6. waitAfter 10 minutes
  7. customthe mixture was removed from ice
  8. customthe layers were separated
  9. additionMore DCM was added
  10. filtrationthe mixture was filtered
  11. customThe organic was separated from the filtrate
  12. customthe combined organic phases were dried
  13. filtrationfiltered
  14. concentrationconcentrated
  15. custompurified through flash column chromatography (eluent
  16. dissolution10% ethyl acetate: hexane, dissolving the sample in 3:1 ethyl acetate

出典と根拠

ORDレコード
ord-e49cc9fa564f42bd8fe1abd405fbc926
出典データセット
uspto-grants-2006_10
特許番号
US07125891B2

反応ノート

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