Triacetoxyperiodinane → HCID 352578, compound

HRID 1393016Notes

Reaction equation

HRID 1393016 reaction equation
[CH3:1][N:2]1[CH2:23][C:8]23[CH2:9][CH2:10][CH:11]4[CH:20]([CH:7]2[CH2:6][CH2:5][CH:4]3[CH:3]1[CH3:24])[CH2:19][CH:18]=[C:17]1[C:12]4([CH3:22])[CH2:13][CH2:14][CH:15]([OH:21])[CH2:16]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH3:1][N:2]1[CH2:23][C:8]23[CH2:9][CH2:10][CH:11]4[CH:20]([CH:7]2[CH2:6][CH2:5][CH:4]3[CH:3]1[CH3:24])[CH2:19][CH:18]=[C:17]1[C:12]4([CH3:22])[CH2:13][CH2:14][C:15](=[O:21])[CH2:16]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67422524HCID 67422524, compound

Product 1

HCID 352578HCID 352578, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of Compound 130A (200 mg, 0.607 mmol) Dess-Martin periodinane (386 mg, 0.91 mmol) and dichloromethane (10 mL) was stirred at room temperature for 4.5 hours. The reaction was quenched with 10% sodium thiosulfate and extracted with dichloromethane. Organic layer was dried over sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give the crude product, which was purified on silica gel column eluted with 0.3% ammonium hydroxide and 3% methanol in dichloromethane to give the desired product (156 mg, 83% yield).

Workup

  1. customThe reaction was quenched with 10% sodium thiosulfate
  2. extractionextracted with dichloromethane
  3. dry with materialOrganic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customto give the crude product, which
  7. customwas purified on silica gel column
  8. washeluted with 0.3% ammonium hydroxide and 3% methanol in dichloromethane

Sources & evidence

ORD record
ord-c7ab71c45fd84d868a5a99a5c11355ce
Source dataset
uspto-grants-2008_03
Patent number
US07345034B2

Reaction notes

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