Triacetoxyperiodinane → HCID 89963244, compound

HRID 337900Notes

Reaction equation

HRID 337900 reaction equation
[C:1]([O:9][C@H:10]1[CH2:14][C@@H:13]([OH:15])[CH2:12][C@@H:11]1[C:16]1[N:20]([CH3:21])[N:19]=[CH:18][CH:17]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])O.[Na+]>ClCCl>[C:1]([O:9][C@H:10]1[CH2:14][C:13](=[O:15])[CH2:12][C@@H:11]1[C:16]1[N:20]([CH3:21])[N:19]=[CH:18][CH:17]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 89962137HCID 89962137, compound

Product 1

HCID 89963244HCID 89963244, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the (1S*,2R*,4S*)-4-hydroxy-2-(1-methyl-1H-pyrazol-5-yl)cyclopentyl benzoate (205 mg, 0.716 mmol) prepared in Example 107b in dichloromethane (3.0 mL), a Dess-Martin reagent (610 mg, 1.44 mmol) was added, and the reaction solution was stirred for 2 hours. To the reaction solution, an aqueous sodium hydrogencarbonate solution (10 mL) was added, and an organic layer was extracted with dichloromethane (10 mL). The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (hexane/ethyl acetate=2:3) to yield the title compound (140 mg, 69%) as a colorless oil.

Workup

  1. extractionan organic layer was extracted with dichloromethane (10 mL)
  2. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
  3. concentrationAfter vacuum concentration
  4. customthe residue was purified with silica gel chromatography (hexane/ethyl acetate=2:3)

Sources & evidence

ORD record
ord-52d1661a8d7a47348d81528e8c2f3bc6
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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