Triacetoxyperiodinane → HCID 67228515, compound

HRID 1515875Notes

Reaction equation

HRID 1515875 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1[CH:9]=[C:10]2[CH:16]=[C:15]([CH:17]([OH:25])[CH2:18][CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[N:14]([S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)(=[O:28])=[O:27])[C:11]2=[N:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1[CH:9]=[C:10]2[CH:16]=[C:15]([C:17](=[O:25])[CH2:18][CH:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)[N:14]([S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)(=[O:27])=[O:28])[C:11]2=[N:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67229027{1-benzenesulfonyl-2-[1-hydroxy-2-(tetrahydro-pyran-4-yl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-carbamic acid tert-butyl ester

Product 1

HCID 67228515HCID 67228515, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of {1-benzenesulfonyl-2-[1-hydroxy-2-(tetrahydro-pyran-4-yl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-carbamic acid tert-butyl ester (1.5 g, 3.0 mmol) in dichloromethane (15 mL) was added Dess-Martin periodinane (4.44 g, 10.4 mmol) at 25° C. The reaction mixture was stirred at 25° C. for 1 h and then quenched with a saturated aqueous sodium bicarbonate solution (20 mL). The mixture was extracted with ethyl acetate (100 mL), washed with a saturated aqueous sodium bicarbonate solution (3×20 mL), brine, dried over anhydrous sodium sulfate and then concentrated in vacuo. The residue was purified by flash column chromatography (silica gel from QingDao, 200-300 mesh, 50% ethyl acetate/hexanes) afforded [1-benzenesulfonyl-2-(2-tetrahydro-pyran-4-yl-acetyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-carbamic acid tert-butyl ester (1.0 g, 67%) as a light yellow solid: LC/MS m/e calcd for C25H29N3O6S [M+H]+ 500.59, observed 500.2.

Workup

  1. customquenched with a saturated aqueous sodium bicarbonate solution (20 mL)
  2. extractionThe mixture was extracted with ethyl acetate (100 mL)
  3. washwashed with a saturated aqueous sodium bicarbonate solution (3×20 mL), brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (silica gel from QingDao, 200-300 mesh, 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-cda563594f7c49b1bc4f3bd1f3c5c8e6
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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