Triacetoxyperiodinane → HCID 86732114, compound

HRID 930285Notes

Reaction equation

HRID 930285 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:20])=[C:6]([C@@:8]([NH:13][S@@:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[O:15])([CH2:10][CH2:11][OH:12])[CH3:9])[CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:20])=[C:6]([C@@:8]([NH:13][S@@:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[O:15])([CH2:10][CH:11]=[O:12])[CH3:9])[CH:7]=1

Participants

3

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86732115HCID 86732115, compound

Product 1

HCID 86732114HCID 86732114, compoundYield 82.5%

Procedure

A 100 mL flask containing (R)-N-((S)-2-(5-Bromo-2-fluorophenyl)-4-hydroxybutan-2-yl)-2-methylpropane-2-sulfinamide (4c, 2.472 g, 6.75 mmol) under nitrogen was placed in a water bath and treated with Dess-Martin periodinane (Aldrich; 0.3 M in CH2Cl2; 25 mL, 7.50 mmol). The mixture was stirred at ambient temperature for 3 h, after which the reaction was quenched with saturated aqueous sodium thiosulfate solution (7.5 mL) and stirred for 15 min. The product was extracted into CH2Cl2 from saturated aqueous NaHCO3, dried over Na2SO4, concentrated, and purified by chromatography on silica gel [Gradient: 20%→100% EtOAc/hexane] to give (R)-N-((S)-2-(5-bromo-2-fluorophenyl)-4-oxobutan-2-yl)-2-methylpropane-2-sulfinamide (2.03 g, 5.57 mmol) as a colorless gum. MS m/z=365.9 [M+H]+. Calculated for C14H19BrFNO2S: 364.3

Workup

  1. customwas placed in a water bath
  2. customafter which the reaction was quenched with saturated aqueous sodium thiosulfate solution (7.5 mL)
  3. stirringstirred for 15 min
  4. extractionThe product was extracted into CH2Cl2 from saturated aqueous NaHCO3
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. custompurified by chromatography on silica gel [Gradient: 20%→100% EtOAc/hexane]

Sources & evidence

ORD record
ord-73692d621c464485ac1ef18e5f9754e2
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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