Sodium Iodide → [(3aR,4R,6R,6aS)-6-(6-iodo-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methyl acetate

HRID 552726Notes

Reaction equation

HRID 552726 reaction equation
[C:1]([O:4][CH2:5][C@@H:6]1[C@@H:13]2[C@@H:9]([O:10][C:11]([CH3:15])([CH3:14])[O:12]2)[C@H:8]([N:16]2[CH:24]=[N:23][C:22]3[C:17]2=[N:18][CH:19]=[N:20][C:21]=3Cl)[CH2:7]1)(=[O:3])[CH3:2].[Na+].[I-:27].FC(F)(F)C(O)=O>CC(=O)CC>[C:1]([O:4][CH2:5][C@@H:6]1[C@@H:13]2[C@@H:9]([O:10][C:11]([CH3:15])([CH3:14])[O:12]2)[C@H:8]([N:16]2[CH:24]=[N:23][C:22]3[C:17]2=[N:18][CH:19]=[N:20][C:21]=3[I:27])[CH2:7]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6422Trifluoroacetic acidHCID 86607316[(3aR,4R,6R,6aS)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methyl acetate

Product 1

HCID 86607317[(3aR,4R,6R,6aS)-6-(6-iodo-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methyl acetateYield 67.9%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of [(3aR,4R,6R,6aS)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methyl acetate (185 mg, 0.45 mmol) in 2-butanone (8 mL) at 0° C. was added NaI (1.36 g, 9.08 mmol) followed by trifluoroacetic acid (174.8 μL, 2.27 mmol). The reaction was stirred for 3 hours at 0° C., quenched with saturated aq NaHCO3 and extracted with DCM. The organic phase was concentrated and the residue was purified by flash chromatography (0 to 100% EtOAc/DCM) to obtain the title compound (140 mg, 67%).

Workup

  1. customquenched with saturated aq NaHCO3
  2. extractionextracted with DCM
  3. concentrationThe organic phase was concentrated
  4. customthe residue was purified by flash chromatography (0 to 100% EtOAc/DCM)

Sources & evidence

ORD record
ord-bf48b60afeab44f496f42d8e52c40c17
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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