Reaktion #60266

Reaktionsgleichung

NMO

6-(4-Bromo-2-methyl-phenylamino)-7-fluoro-3-pent-4-enyl-3H-benzoimidazole-5-carboxylic acid cyclopropylmethoxy-amide

t-BuOH

→

pure desired product

Ausbeute 74.0%

6-(4-Bromo-2-methyl-phenylamino)-3-(4,5-dihydroxy-pentyl)-7-fluoro-3H-benzoimidazole-5-carboxylic acid cyclopropylmethoxy-amide

Ausbeute 74.0%

Lösungsmittel

THF water

OsO4

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONadded
2. 2
   Sonstigethe reaction mixture is quenched by the addition of 10% NaHS2O3 solution
3. 3
   workup.WAITAfter 10 minutes
4. 4
   Filtrationthe reaction mixture is filtered through Celite
5. 5
   Waschenrinsing with ethyl acetate and methylene chloride
6. 6
   workup.ADDITIONThe filtrate is diluted with ethyl acetate
7. 7
   Waschenwashed with 0.01 N HCl, and brine
8. 8
   TrocknenThe organic layer is dried (Na2SO4)
9. 9
   Einengenconcentrated under reduced pressure
10. 10
    SonstigeThe crude product is purified by FCC
11. 11
    Wascheneluted with 9:1 ethyl acetate/MeOH

Vorschrift

6-(4-Bromo-2-methyl-phenylamino)-7-fluoro-3-pent-4-enyl-3H-benzoimidazole-5-carboxylic acid cyclopropylmethoxy-amide 11f (0.307 g, 0.612 mmol) is dissolved in 4:1 THF/water (8 mL) and 1.134 mL (0.061 mmol) of an 0.054 M OsO4 solution in t-BuOH iias added followed by NMO (0.093 g, 0.796 mmol). After 5 hours, the reaction mixture is quenched by the addition of 10% NaHS2O3 solution. After 10 minutes, the reaction mixture is filtered through Celite rinsing with ethyl acetate and methylene chloride. The filtrate is diluted with ethyl acetate and washed with 0.01 N HCl, and brine. The organic layer is dried (Na2SO4) and concentrated under reduced pressure. The crude product is purified by FCC eluted with 9:1 ethyl acetate/MeOH to give 0.244 g (74%) pure desired product.

Quelle