Triacetoxyperiodinane → HCID 57857058, compound

HRID 561771Notes

Reaction equation

HRID 561771 reaction equation
[Si:1]([O:8][C@@H:9]([CH:31]1[CH2:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:32]1)/[CH:10]=[CH:11]/[C@H:12]1[C@@H:16]([F:17])[CH2:15][C:14](=[O:18])[C@@H:13]1[CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][C:25]([O:27]C(C)C)=[O:26])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Si:1]([O:8][C@@H:9]([CH:31]1[CH2:32][C:33]2[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:39]1)/[CH:10]=[CH:11]/[C@H:12]1[C@@H:16]([F:17])[CH2:15][C:14](=[O:18])[C@@H:13]1[CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57857056HCID 57857056, compound

Product 1

HCID 57857058HCID 57857058, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring mixture consisting of (Z)-isopropyl 7-((1R,2R,3S)-2-((S,E)-3-(tert-butyldimethylsilyloxy)-3-(2,3-dihydro-1H-inden-2-yl)prop-1-enyl)-3-fluoro-5-oxocyclopentyl)hept-5-enoate (prepared in Step L, 580 mg) in DCM (30 mL) at room temperature was added Dess-Martin reagent (1.5 g) and the reaction mixture was stirred for 3 hours. The mixture was concentrated under reduced pressure and the residue was redissolved in diethyl ether. The insoluble materials were removed by filtration. The crude product in diethyl ether was applied to a silica gel column. Elution with hexanes-ethyl acetate (4:1 with 0.4% acetic acid) afforded the title intermediate (522 mg, 89%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue was redissolved in diethyl ether
  3. customThe insoluble materials were removed by filtration
  4. washElution with hexanes-ethyl acetate (4:1 with 0.4% acetic acid)

Sources & evidence

ORD record
ord-f176494860964c7c8fe7a7e0054c7c61
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

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