Triacetoxyperiodinane → HCID 67229036, compound

HRID 1515786Notes

Reaction equation

HRID 1515786 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=[C:11]2[CH:19]([OH:30])[CH2:20][CH:21]2[CH2:29][CH2:28][C:23]3([O:27][CH2:26][CH2:25][O:24]3)[CH2:22]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=[C:11]2[C:19](=[O:30])[CH2:20][CH:21]2[CH2:29][CH2:28][C:23]3([O:27][CH2:26][CH2:25][O:24]3)[CH2:22]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67229703HCID 67229703, compound

Product 1

HCID 67229036HCID 67229036, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(1,4-dioxa-spiro[4.4]non-7-yl)-ethanol (2.5 g, 5.84 mmol) in dichloromethane (150 mL) was added Dess-Martin periodinane (6.2 g, 14.6 mmol) at 25° C. The reaction mixture was stirred at 25° C. for 2 h and then quenched with a saturated aqueous sodium bicarbonate solution (100 mL). The mixture was extracted with dichloromethane (50 mL), washed with a saturated aqueous sodium bicarbonate solution (3×100 mL), brine, dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by flash column chromatography (QingDao silica gel, 200-300 mesh, 50% ethyl acetate/hexanes) afforded 1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(1,4-dioxa-spiro[4.4]non-7-yl)-ethanone (2.45 g, 98%) as a light yellow solid: LC/MS m/e calcd for C22H22N2O5S [M+H]+ 427.50, observed 427.5.

Workup

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

Sources & evidence

ORD record
ord-12871f6a3c1a4e23a837207268c6429d
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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