Triacetoxyperiodinane → HCID 86636648, compound

HRID 1361324Notes

Reaction equation

HRID 1361324 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][C@H:10]([N:13]([CH:22]2[CH2:27][CH2:26][C:25]([CH3:29])([CH3:28])[CH2:24][CH2:23]2)[C:14](=[O:21])[C:15]([CH3:20])([CH3:19])[CH:16]([OH:18])[CH3:17])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([N:8]1[CH2:12][CH2:11][C@H:10]([N:13]([CH:22]2[CH2:27][CH2:26][C:25]([CH3:29])([CH3:28])[CH2:24][CH2:23]2)[C:14](=[O:21])[C:15]([CH3:19])([CH3:20])[C:16](=[O:18])[CH3:17])[CH2:9]1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66971107HCID 66971107, compound

Product 1

HCID 86636648HCID 86636648, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3S)-1-Boc-3-[(4,4-dimethylcyclohexyl)(3-hydroxy-2,2-dimethylbutanoyl)amino]pyrrolidine (150 mg, 0.36 mmol) prepared in Step A of Example C4 in DCM was added Dess-Martin periodinane (230 mg, 0.54 mmol), and stirred at rt for 2 h. After the reaction finished, the solvent was concentrated in vacuo, sodium thiosulfate aqueous solution and EtOAc were added and stirred at rt for 30 min, and extracted with EtOAc. The organic layer was dried over MgSO4, concentrated in vacuo at rt, and purified by column chromatography (eluent: EtOAc/Hex=1/3) to give the title compound (132 mg, 90%).

Workup

  1. concentrationthe solvent was concentrated in vacuo, sodium thiosulfate aqueous solution and EtOAc
  2. additionwere added
  3. stirringstirred at rt for 30 min
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo at rt
  7. custompurified by column chromatography (eluent: EtOAc/Hex=1/3)

Sources & evidence

ORD record
ord-a9cebe4eaf4d4e46a632473e15e2b72e
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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