Triacetoxyperiodinane → HCID 86636647, compound

HRID 1361321Notes

Reaction equation

HRID 1361321 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][C@H:10]([N:13]([CH:21]2[CH2:26][CH2:25][C:24]([CH3:28])([CH3:27])[CH2:23][CH2:22]2)[C:14](=[O:20])[C:15]([CH3:19])([CH3:18])[CH2:16][OH: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:21]2[CH2:26][CH2:25][C:24]([CH3:28])([CH3:27])[CH2:23][CH2:22]2)[C:14](=[O:20])[C:15]([CH3:19])([CH3:18])[CH:16]=[O:17])[CH2:9]1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66971267HCID 66971267, compound

Product 1

HCID 86636647HCID 86636647, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3S)-1-Boc-3-[(4,4-dimethylcyclohexyl)(3-hydroxy-2,2-dimethylpropanoyl)amino]pyrrolidine (1.05 g, 2.7 mmol) prepared in Step B of Example A8 in DCM was added Dess-Martin periodinane (1.35 g, 3.17 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 (960 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-8b9ee407ffef4c19938b603ddc4f7198
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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