TBAF tetrahydrofuran → 2-Bromo-1-[3-hydroxy-2-(tetrahydropyran-2-yloxy)propyl]-4-nitroimidazole

To tetrahydrofuran (120 ml) solution of 2-bromo-1-[3-(t-butyldimethylsilanyloxy)-2-(tetrahydropyran-2-yloxy)propyl)-4-nitroimidazole (12.7 g) prepared in Example 28, was added 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (30 ml) under stirring and ice-cooling condition, the reaction mixture was stirred at a room temperature overnight. The reaction mixture was concentrated under a reduced pressure and the residue was diluted with ethyl acetate, washed with water and an aqueous solution being saturated with sodium chloride. After being dried over anhydrous magnesium sulfate, the residue was concentrated under a reduced pressure, thus obtained residue was purified by use of a silica gel column chromatography (eluent: dichloromethane/ethyl acetate=10/1), there was obtained 2-bromo-1-[3-hydroxy-2-(tetrahydropyran-2-yloxy)propyl]-4-nitroimidazole (8.51 g, yield: 89%) as colorless liquid product.

1. temperatureice-cooling condition
2. stirringthe reaction mixture was stirred at a room temperature overnight
3. concentrationThe reaction mixture was concentrated under a reduced pressure
4. additionthe residue was diluted with ethyl acetate
5. washwashed with water
6. dry with materialAfter being dried over anhydrous magnesium sulfate
7. concentrationthe residue was concentrated under a reduced pressure, thus obtained residue
8. customwas purified by use of a silica gel column chromatography (eluent: dichloromethane/ethyl acetate=10/1)

ORD record

ord-2c04f23bc4244cf6929cb34dc84e5e28

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129544B2