Water → HCID 86618261, compound

HRID 1159825Notes

Reaction equation

HRID 1159825 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:22]=C)=[C:13]2[C:17]=1[N:16]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.I([O-])(=O)(=O)=[O:33].[Na+].O>O1CCOCC1.[Os](=O)(=O)(=O)=O>[CH2:1]([O:8][C:9]1[C:17]2[N:16]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:15]=[CH:14][C:13]=2[C:12]([CH:22]=[O:33])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 68716616HCID 68716616, compound2×

Product 1

HCID 86618261HCID 86618261, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 7-benzyloxy-1-methanesulfonyl-4-vinyl-1H-indole (1.3 g, 3.9 mmol; Intermediate 84) in dioxane (25 ml), lutidine (900 μl, 7.9 mmol), sodium metaperiodate (3.37 g, 15.8 mmol) (in water (10 ml)) and osmium tetroxide (100 mg, 0.1 mmol) was added (in that order). A precipitate was almost immediately formed, and the mixture was stirred for 1 h at room temperature. Water was added. The precipitate was filtered off, and washed with water. The solid material was extracted with acetonitrile. The acetonitrile-solution was evaporated. The product was purified by strait phase chromatography using Biotage flash-chromatograph 5-40% EtOAc in petroleum ether 40-60° C. Obtained 0.40 mg. MS (ESI+) for C17H15NO4S m/z 330 (M+H)+.

Workup

  1. customA precipitate was almost immediately formed
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. extractionThe solid material was extracted with acetonitrile
  5. customThe acetonitrile-solution was evaporated
  6. customThe product was purified by strait phase chromatography
  7. customBiotage flash-chromatograph 5-40% EtOAc in petroleum ether 40-60° C
  8. customObtained 0.40 mg

Sources & evidence

ORD record
ord-24914b8afb874fb68339570f258d38e0
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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