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

HRID 215856ノート

反応式

HRID 215856 の反応式
[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

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 656671Sodium PyrosulfiteHCID 23667635Sodium periodateHCID 86643670HCID 86643670、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 61850Ruthenium trichloride触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f73be1695a244856b9cdda36e038daed
出典データセット
uspto-grants-2012_06
特許番号
US08193164B2

反応ノート

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