Triacetoxyperiodinane → HCID 21914148, compound

HRID 551391Notes

Reaction equation

HRID 551391 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

Bis(1,1-dimethylethyl)ester dicarbonic acid (0.07615 mol) in DCM (50 ml) was added over 5 minutes to 2,3-dihydro-1H-indole-2-methanol (0.07615 mol) in DCM (150 ml) at 0° C. The mixture was allowed to warm to room temperature and stirred overnight. The mixture was concentrated under reduced pressure and submitted to a Kogel Rohr distillation, yielding 11.98 g of 1,1-dimethylethyl 2,3-dihydro-2-(hydroxymethyl)-1H-indole-1-carboxylate (intermediate 11). b) 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-3807ee54bf3a40a4b49beb3fe0e3afef
Source dataset
uspto-grants-2011_05
Patent number
US07947713B2

Reaction notes

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