Ethyl Acetate → 3-(2,6-Dichloro-purin-9-yl)-5-(4-ethyl-[1,2,3]triazol-1-yl)-cyclopentane-1,2-diol

HRID 215856Notes

Reaction equation

HRID 215856 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([N:16]3[CH:20]=[C:19]([CH2:21][CH3:22])[N:18]=[N:17]3)C=C2)=[C:4]([Cl:23])[N:3]=1.I([O-])(=O)(=O)=O.[Na+].S(S([O-])=O)([O-])(=O)=[O:31].[Na+].[Na+].CCO[C:42]([CH3:44])=[O:43]>CC#N.O.[Ru](Cl)(Cl)Cl>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:15][CH:14]([N:16]3[CH:20]=[C:19]([CH2:21][CH3:22])[N:18]=[N:17]3)[CH:44]([OH:31])[CH:42]2[OH:43])=[C:4]([Cl:23])[N:3]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 656671Sodium PyrosulfiteHCID 23667635Sodium periodateHCID 86643670HCID 86643670, compound

Product 1

HCID 866436713-(2,6-Dichloro-purin-9-yl)-5-(4-ethyl-[1,2,3]triazol-1-yl)-cyclopentane-1,2-diol

Reagents, catalysts & solvents 3

HCID 61850Ruthenium trichlorideCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 2,6-dichloro-9-[(1R,4S)-4-(4-ethyl-[1,2,3]triazol-1-yl)-cyclopent-2-enyl]-9H-purine (1.442 g, 4.12 mmol) in EtOAc (15 mL) and MeCN (15 mL) is treated with a solution of ruthenium trichloride (0.120 g, 0.58 mmol) and sodium periodate (1.32 g, 6.18 mmol) in water (5 mL). The reaction mixture is stirred vigorously for 6 hours and then treated with sodium metabisulfite (saturated aqueous solution, 25 mL) and then stirred overnight. The resulting mixture is partitioned between water and EtOAc and the aqueous portion is extracted with EtOAc. The combined organic portions are washed with water, dried (MgSO4) and concentrated in vacuo. The crude product is purified by chromatography on silica eluting with 0-100% EtOAc in iso-hexane to afford the title compound as an oil orange solid. (MH+ 350).

Workup

  1. stirringstirred overnight
  2. customThe resulting mixture is partitioned between water and EtOAc
  3. extractionthe aqueous portion is extracted with EtOAc
  4. washThe combined organic portions are washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by chromatography on silica eluting with 0-100% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-f73be1695a244856b9cdda36e038daed
Source dataset
uspto-grants-2012_06
Patent number
US08193164B2

Reaction notes

Loading…