Triacetoxyperiodinane → HCID 21914148, compound

HRID 887913Notes

Reaction equation

HRID 887913 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

HCID 21914148HCID 21914148, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-b8089c30c42a40e0b01c0060df7e33bc
Source dataset
uspto-grants-2012_08
Patent number
US08247432B2

Reaction notes

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